HCID 21138123, compound → HCID 86585312, compound

HRID 1358874Notes

Reaction equation

HRID 1358874 reaction equation
[C:1]([O-])(=[S:3])[CH3:2].[K+].I[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@H:20]2[CH2:37][C@@:35]3([CH3:36])[C@@H:31]([CH2:32][CH2:33][C@@H:34]3[OH:38])[C@H:30]3[C@H:21]2[C:22]2[CH:23]=[CH:24][C:25]([OH:39])=[CH:26][C:27]=2[CH2:28][CH2:29]3)=[CH:16][CH:15]=1>C(O)C>[C:1]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@H:20]2[CH2:37][C@@:35]3([CH3:36])[C@@H:31]([CH2:32][CH2:33][C@@H:34]3[OH:38])[C@H:30]3[C@H:21]2[C:22]2[CH:23]=[CH:24][C:25]([OH:39])=[CH:26][C:27]=2[CH2:28][CH2:29]3)=[CH:16][CH:15]=1)(=[S:3])[CH3:2]

Participants

4

Reactant 2

HCID 21138123HCID 21138123, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 86585312HCID 86585312, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

150 mg of potassium thioacetate is added to a solution of 470 mg of the product obtained in Stage D in 6 cm3 of ethanol and agitation is carried out for 1 hour 50 minutes at 50° C. The ethanol is distilled off, the residue is taken up in ethyl acetate, washed with water, dried and evaporated to dryness under reduced pressure. 400 mg of residue is obtained which is chromatographed on silica (eluant ethyl acetate-essence G 6/4 then 8/2). 265 mg of desired product is collected (M.p. #90° C.).

Workup

  1. distillationThe ethanol is distilled off
  2. washwashed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c9a4c40926e24464893b81abb8bee75c
Source dataset
uspto-grants-2003_07
Patent number
US06596885B2

Reaction notes

Loading…