nonane-1-thiol

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

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

Procedure: Using the procedure of Example 4 with 30 g of 5-chloro-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole and 17.6 g of nonyl mercaptan, the title compound is prepared.

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

Procedure: Using the procedure of Example 4 with 30 g of 5-chloro-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole and 17.6 g of nonyl mercaptan, the title compound is prepared.

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

Procedure: Using the procedure of Example 4 with 30 g of 5-chloro-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole and 17.6 g of nonyl mercaptan, the title compound is prepared.

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

Procedure: 6.2 g of the title compound was prepared from 10 g of 3-(1,3-benzodioxol-5-yl)propanethiol and 5 g of nonyl mercaptan as a colorless oil according to the same procedure as that described in Example 1.

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

Procedure: 6.2 g of the title compound was prepared from 10 g of 3-(1,3-benzodioxol-5-yl)propanethiol and 5 g of nonyl mercaptan as a colorless oil according to the same procedure as that described in Example 1.

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

Procedure: Using the procedure of Example 4 with 30 g of 5-chloro-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole and 17.6 g of nonyl mercaptan, the title compound is prepared.

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

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

Procedure: Treatment of 6 (17) [(5S), 458 mg, 2.58 mmol] in dry DMF (3 mL) with thiolate solution in dry DMF (7 mL) generated from nonanethiol (510 μL, 433 mg, 2.71 mmol), and NaH (114 mg, 2.84 mmol, 60%/mineral oil) in dry DMF (7 mL) by Procedure A [column chromatography (80% EtOAc/hexane→EtOAc)] gave 7c(5S) (652 mg, 98%) as a colorless oil: 1H NMR δ 0.86 (t, J=7.0 Hz, 3H), 1.19-1.29 (m, 10H), 1.29-1.38 (m, 2H), 1.54 (‘quint’, J=7.3 Hz, 2H), 1.75-1.85 (m, 1H), 2.23-2.43 (m, 3H), 2.51 (t, J=7.5 Hz, 2H), 2.54 (dd, J=7.4, 13.2 Hz, 1H), 2.65 (dd, J=5.8, 13.2 Hz, 1H), 3.78 (‘quint’, J=6.5 Hz, 1H), 6.97 (br. s, 1H); 13C NMR δ 14.1, 22.6, 26.6, 28.8, 29.2, 29.2, 29.4, 29.8, 30.1, 31.8, 32.7, 38.6, 53.9, 178.0; MS (ESI) m/z 258 (100, M+). gave 7c(5S) (652 mg, 98%) as a colorless oil

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

Procedure: 2 ml of a 30% solution of sodium methoxide in methanol were added to a solution of 2 ml of nonanethiol in a 20 ml methanol/5 ml THF mixture, under an inert atmosphere. The mixture was maintained under stirring for 30 min and then added to a solution of 2 g of methyl 7-chloro-3-thia-5-heptynoate in 20 ml of methanol, under an inert atmosphere. The mixture was maintained under stirring for 15 hours at room temperature and then the reaction medium was poured over 100 ml of acid water (98 ml of water+2 ml concentrated H2SO4) and then extracted 3 times with ethyl ether. The combined organic phases were washed 3 times with water and then with a saturated aqueous solution of NaCl before being dried (Na2SO4), filtered and concentrated under vacuum in a rotary evaporator. The oil thus obtained was chromatographed on a silica gel column (CH2Cl2/heptane 85/15) providing 2.1 g of methyl 3,8-dithia-5-heptadecynoate in the form of an orange-colored oil (yield 64%). The mixture was maintained The mixture was maintained under stirring for 15 hours at room temperature extracted 3 times with ethyl ether The combined organic phases were washed 3 times with water with a saturated aqueous solution of NaCl before being dried (Na2SO4) filtered concentrated under vacuum in a rotary evaporator The oil thus obtained was chromatographed on a silica gel column (CH2Cl2/heptane 85/15)

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

Procedure: Using the procedure of Example 4 with 30 g of 5-chloro2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole and 17.6 g of nonyl mercaptan, the title compound is prepared.

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

Procedure: Using the procedure of Example 4 with 30 g of 5-chloro-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole and 17.6 g of nonyl mercaptan, the title compound is prepared.