8-chloro-2,2-dimethyl-3,4-dihydrochromene-6-carbaldehyde

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vial was charged with Pd(OAc)2 (7.99 mg, 0.04 mmol), XPhos (25.5 mg, 0.05 mmol), potassium carbonate (148 mg, 1.07 mmol), potassium cyclopropyltrifluoroborate (58.0 mg, 0.39 mmol) and 8-chloro-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbaldehyde (80 mg, 0.36 mmol). The mixture was dissolved in cyclopropylmethyl ether (1.62 mL) and water (0.16 mL) and purged with Ar. The reaction mixture was then stirred at 100° C. overnight, cooled to room temperature and filtered through a pad of celite. The filtrate was concentrated under vacuum, and the crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes to afford the desired product as a pale-yellow oil. water (0.16 mL) and purged with Ar cooled to room temperature filtered through a pad of celite The filtrate was concentrated under vacuum the crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Bromo-8-chloro-2,2-dimethyl-3,4-dihydro-2H-chromene (483 mg, 1.75 mmol) in THF (8.76 mL) was cooled to −78° C. and n-BuLi (841 μL, 2.10 mmol) was added dropwise via a syringe. The reaction mixture was stirred at −78° C. for 10 minutes and then DMF (543 μL, 7.01 mmol) was added dropwise via a syringe. The resulting mixture was allowed to warm to room temperature, and wet silica gel (5.0 g/0.5 mL of water) was added. The mixture was allowed to stir at room temperature for 10 minutes before it was filtered. The silica gel was rinsed with EtOAc, and the filtrate was concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-15% EtOAc/hexanes to obtain the desired product as a pale-yellow oil. to warm to room temperature wet silica gel (5.0 g/0.5 mL of water) was added to stir at room temperature for 10 minutes before it was filtered The silica gel was rinsed with EtOAc the filtrate was concentrated under vacuum The crude mixture was purified by silica gel chromatography eluting with 0-15% EtOAc/hexanes

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vial was charged with Pd(OAc)2 (7.99 mg, 0.04 mmol), XPhos (25.5 mg, 0.05 mmol), potassium carbonate (148 mg, 1.07 mmol), potassium cyclopropyltrifluoroborate (58.0 mg, 0.39 mmol) and 8-chloro-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbaldehyde (80 mg, 0.36 mmol). The mixture was dissolved in cyclopropylmethyl ether (1.62 mL) and water (0.16 mL) and purged with Ar. The reaction mixture was then stirred at 100° C. overnight, cooled to room temperature and filtered through a pad of celite. The filtrate was concentrated under vacuum, and the crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes to afford the desired product as a pale-yellow oil. water (0.16 mL) and purged with Ar cooled to room temperature filtered through a pad of celite The filtrate was concentrated under vacuum the crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vial was charged with Pd(OAc)2 (7.99 mg, 0.04 mmol), XPhos (25.5 mg, 0.05 mmol), potassium carbonate (148 mg, 1.07 mmol), potassium cyclopropyltrifluoroborate (58.0 mg, 0.39 mmol) and 8-chloro-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbaldehyde (80 mg, 0.36 mmol). The mixture was dissolved in cyclopropylmethyl ether (1.62 mL) and water (0.16 mL) and purged with Ar. The reaction mixture was then stirred at 100° C. overnight, cooled to room temperature and filtered through a pad of celite. The filtrate was concentrated under vacuum, and the crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes to afford the desired product as a pale-yellow oil. water (0.16 mL) and purged with Ar cooled to room temperature filtered through a pad of celite The filtrate was concentrated under vacuum the crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Bromo-8-chloro-2,2-dimethyl-3,4-dihydro-2H-chromene (483 mg, 1.75 mmol) in THF (8.76 mL) was cooled to −78° C. and n-BuLi (841 μL, 2.10 mmol) was added dropwise via a syringe. The reaction mixture was stirred at −78° C. for 10 minutes and then DMF (543 μL, 7.01 mmol) was added dropwise via a syringe. The resulting mixture was allowed to warm to room temperature, and wet silica gel (5.0 g/0.5 mL of water) was added. The mixture was allowed to stir at room temperature for 10 minutes before it was filtered. The silica gel was rinsed with EtOAc, and the filtrate was concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-15% EtOAc/hexanes to obtain the desired product as a pale-yellow oil. to warm to room temperature wet silica gel (5.0 g/0.5 mL of water) was added to stir at room temperature for 10 minutes before it was filtered The silica gel was rinsed with EtOAc the filtrate was concentrated under vacuum The crude mixture was purified by silica gel chromatography eluting with 0-15% EtOAc/hexanes

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vial was charged with Pd(OAc)2 (7.99 mg, 0.04 mmol), XPhos (25.5 mg, 0.05 mmol), potassium carbonate (148 mg, 1.07 mmol), potassium cyclopropyltrifluoroborate (58.0 mg, 0.39 mmol) and 8-chloro-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbaldehyde (80 mg, 0.36 mmol). The mixture was dissolved in cyclopropylmethyl ether (1.62 mL) and water (0.16 mL) and purged with Ar. The reaction mixture was then stirred at 100° C. overnight, cooled to room temperature and filtered through a pad of celite. The filtrate was concentrated under vacuum, and the crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes to afford the desired product as a pale-yellow oil. water (0.16 mL) and purged with Ar cooled to room temperature filtered through a pad of celite The filtrate was concentrated under vacuum the crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Bromo-8-chloro-2,2-dimethyl-3,4-dihydro-2H-chromene (483 mg, 1.75 mmol) in THF (8.76 mL) was cooled to −78° C. and n-BuLi (841 μL, 2.10 mmol) was added dropwise via a syringe. The reaction mixture was stirred at −78° C. for 10 minutes and then DMF (543 μL, 7.01 mmol) was added dropwise via a syringe. The resulting mixture was allowed to warm to room temperature, and wet silica gel (5.0 g/0.5 mL of water) was added. The mixture was allowed to stir at room temperature for 10 minutes before it was filtered. The silica gel was rinsed with EtOAc, and the filtrate was concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-15% EtOAc/hexanes to obtain the desired product as a pale-yellow oil. to warm to room temperature wet silica gel (5.0 g/0.5 mL of water) was added to stir at room temperature for 10 minutes before it was filtered The silica gel was rinsed with EtOAc the filtrate was concentrated under vacuum The crude mixture was purified by silica gel chromatography eluting with 0-15% EtOAc/hexanes