Ethanethiol → (2R,4R)-2-(4-hydroxyphenyl)-4-decanolide

HRID 346085Notes

Reaction equation

HRID 346085 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C(S)C.C[O:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:21][C@@H:20]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[O:19][C:17]2=[O:18])=[CH:12][CH:11]=1.C(=O)(O)[O-].[Na+]>ClCCl>[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:21][C@@H:20]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[O:19][C:17]2=[O:18])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 15653385(2R,4R)-2-(4-methoxyphenyl)-4-decanolide

Product 1

HCID 15653390(2R,4R)-2-(4-hydroxyphenyl)-4-decanolideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.6 g of aluminium chloride and 2 ml of ethanethiol in 15 ml of dichloromethane was added, at 0° C, a solution of 440 mg of (2R,4R)-2-(4-methoxyphenyl)-4-decanolide dissolved in 5 ml of dichloromethane. This mixture was stirred for 4 hours. A saturated sodium bicarbonate aq. solution was then added, and the resulting mixture was subjected to extraction with dichloromethane, followed by column chromatography (Kieselgel 60, hexane/ethyl acetate = 3/1), thereby obtaining 374 mg (yield 90%) of (2R,4R)-2-(4-hydroxyphenyl)-4-decanolide. Identification data for this product are as follows. Melting point 87-88° C. [α]D20 +3.2° (c=1.27, MeOH).

Workup

  1. extractionthe resulting mixture was subjected to extraction with dichloromethane

Sources & evidence

ORD record
ord-8839cfe2905642dfa7012ec04123205a
Source dataset
uspto-grants-1991_10
Patent number
US05061398

Reaction notes

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