3,4-dihydro-2H-thiochromen-4-ol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Reduction of thiochroman-4-one with lithium aluminum hydride by the method of Preparation O, Part (iii), affords thiochroman-4-ol in like manner. This is taken up in acetic acid containing a molar excess of acetic anhydride, the mixture heated at reflux for three hours, cooled, ethanol added to quench the excess anhydride and the mixture hydrogenated by the method of Example 11.

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

Procedure: Reduction of thiochroman-4-one with lithium aluminum hydride by the method of Preparation O, Part (iii), affords thiochroman-4-ol in like manner. This is taken up in acetic acid containing a molar excess of acetic anhydride, the mixture heated at reflux for three hours, cooled, ethanol added to quench the excess anhydride and the mixture hydrogenated by the method of Example 11.

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

Procedure: A solution of thiochroman-4-one (9 g) in ether (27 ml) was added slowly to a mixture of lithium aluminium hydride (0.53 g) in ether (54 ml). After the end of the addition, the mixture was refluxed for 2 hours. The reaction mixture was cooled and ice was added, followed by water and by a solution of 20% H2SO4. The water phase was washed twice with ether. The ether phase was washed twice with NaOH 2N, and once with water, dried over MgSO4 and evaporated. The clear oil (8.9 g) crystallised after few hours. Rdt=97% After the end of the addition the mixture was refluxed for 2 hours The reaction mixture was cooled ice was added The water phase was washed twice with ether The ether phase was washed twice with NaOH 2N once with water, dried over MgSO4 evaporated The clear oil (8.9 g) crystallised after few hours

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

Procedure: A solution of thiochroman-4-one (9 g) in ether (27 ml) was added slowly to a mixture of lithium aluminium hydride (0.53 g) in ether (54 ml). After the end of the addition, the mixture was refluxed for 2 hours. The reaction mixture was cooled and ice was added, followed by water and by a solution of 20% H2SO4. The water phase was washed twice with ether. The ether phase was washed twice with NaOH 2N, and once with water, dried over MgSO4 and evaporated. The clear oil (8.9 g) crystallised after few hours. Rdt=97% After the end of the addition the mixture was refluxed for 2 hours The reaction mixture was cooled ice was added The water phase was washed twice with ether The ether phase was washed twice with NaOH 2N once with water, dried over MgSO4 evaporated The clear oil (8.9 g) crystallised after few hours

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

Procedure: Reduction of thiochroman-4-one with lithium aluminum hydride by the method of Preparation O, Part (iii), affords thiochroman-4-ol in like manner. This is taken up in acetic acid containing a molar excess of acetic anhydride, the mixture heated at reflux for three hours, cooled, ethanol added to quench the excess anhydride and the mixture hydrogenated by the method of Example 11.

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of thiochroman-4-one (9 g) in ether (27 ml) was added slowly to a mixture of lithium aluminium hydride (0.53 g) in ether (54 ml). After the end of the addition, the mixture was refluxed for 2 hours. The reaction mixture was cooled and ice was added, followed by water and by a solution of 20% H2SO4. The water phase was washed twice with ether. The ether phase was washed twice with NaOH 2N, and once with water, dried over MgSO4 and evaporated. The clear oil (8.9 g) crystallised after few hours. Rdt=97% After the end of the addition the mixture was refluxed for 2 hours The reaction mixture was cooled ice was added The water phase was washed twice with ether The ether phase was washed twice with NaOH 2N once with water, dried over MgSO4 evaporated The clear oil (8.9 g) crystallised after few hours

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

Procedure: A solution of thiochroman-4-one (9 g) in ether (27 ml) was added slowly to a mixture of lithium aluminium hydride (0.53 g) in ether (54 ml). After the end of the addition, the mixture was refluxed for 2 hours. The reaction mixture was cooled and ice was added, followed by water and by a solution of 20% H2SO4. The water phase was washed twice with ether. The ether phase was washed twice with NaOH 2N, and once with water, dried over MgSO4 and evaporated. The clear oil (8.9 g) crystallised after few hours. Rdt=97% After the end of the addition the mixture was refluxed for 2 hours The reaction mixture was cooled ice was added The water phase was washed twice with ether The ether phase was washed twice with NaOH 2N once with water, dried over MgSO4 evaporated The clear oil (8.9 g) crystallised after few hours

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

Procedure: A solution of thiochroman-4-one (9 g) in ether (27 ml) was added slowly to a mixture of lithium aluminium hydride (0.53 g) in ether (54 ml). After the end of the addition, the mixture was refluxed for 2 hours. The reaction mixture was cooled and ice was added, followed by water and by a solution of 20% H2SO4. The water phase was washed twice with ether. The ether phase was washed twice with NaOH 2N, and once with water, dried over MgSO4 and evaporated. The clear oil (8.9 g) crystallised after few hours. Rdt=97% After the end of the addition the mixture was refluxed for 2 hours The reaction mixture was cooled ice was added The water phase was washed twice with ether The ether phase was washed twice with NaOH 2N once with water, dried over MgSO4 evaporated The clear oil (8.9 g) crystallised after few hours

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

Procedure: A solution of thiochroman-4-one (9 g) in ether (27 ml) was added slowly to a mixture of lithium aluminium hydride (0.53 g) in ether (54 ml). After the end of the addition, the mixture was refluxed for 2 hours. The reaction mixture was cooled and ice was added, followed by water and by a solution of 20% H2SO4. The water phase was washed twice with ether. The ether phase was washed twice with NaOH 2N, and once with water, dried over MgSO4 and evaporated. The clear oil (8.9 g) crystallised after few hours. Rdt=97% After the end of the addition the mixture was refluxed for 2 hours The reaction mixture was cooled ice was added The water phase was washed twice with ether The ether phase was washed twice with NaOH 2N once with water, dried over MgSO4 evaporated The clear oil (8.9 g) crystallised after few hours

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

Procedure: Reduction of thiochroman-4-one with lithium aluminum hydride by the method of Preparation O, Part (iii), affords thiochroman-4-ol in like manner. This is taken up in acetic acid containing a molar excess of acetic anhydride, the mixture heated at reflux for three hours, cooled, ethanol added to quench the excess anhydride and the mixture hydrogenated by the method of Example 11.