Benzyl Alcohol → Benzyl 4-mercaptobutyrate

HRID 2271031Notes

Reaction equation

[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]1(=[S:16])[O:15][CH2:14][CH2:13][CH2:12]1.O>O1CCCC1>[SH:16][CH2:11][CH2:12][CH2:13][C:14]([O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% in oil dispersion, 1.22 g, 50.9 mmol) was washed with dry tetrahydrofuran (20 ml×3) under nitrogen atomosphere. Freshly distilled tetrahydrofuran (50 ml) was added and the mixture was cooled to 0° C. with an ice bath. To this mixture was added portionwise solution of benzyl alcohol (5 g, 46.2 mmol) in dry tetrahydrofuran (10 ml) and the mixture was stirred for 1 hour at said temperature. To the resulting mixture was added γ-thiobutyrolactone (5.2 g, 50.9 mmol) slowly and the resulting mixture was warmed to room temperature. After stirring for 1 hour, H2O (30 ml) was added carefully and tetrahydrofuran was removed under reduced pressure. The residue was extracted three times with AcOEt. The organic layers were combined, washed with brine, and dried over magnesium sulfate. The solvent was evaporated to give 9.96 g of benzyl 4-mercaptobutyrate as a colorless oil which was taken to the next step without further purification.

Workup

temperaturethe resulting mixture was warmed to room temperature
stirringAfter stirring for 1 hour
customtetrahydrofuran was removed under reduced pressure
extractionThe residue was extracted three times with AcOEt
washwashed with brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated

Sources & evidence

ORD record: ord-ec780771bf154a0f84ac4709a5e2086b
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06333324B1

Reaction notes

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