Diethyl Ether → HCID 20355554, compound

HRID 371653Notes

Reaction equation

HRID 371653 reaction equation
[S:1]1C=CC=C1CC(O)=O.[CH2:10]([O:17][CH2:18][CH:19]([O:22][C:23](=[O:25])[CH3:24])[CH:20]=[CH2:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:26][CH2:27][O:28]CC>>[C:27]([S:1][CH2:21][CH2:20][CH:19]([O:22][C:23](=[O:25])[CH3:24])[CH2:18][O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:28])[CH3:26]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 159702-Thiopheneacetic acidHCID 20355562HCID 20355562, compound

Product 1

HCID 20355554HCID 20355554, compoundYield 64%

Procedure

A solution of thiolacetic acid (10.0 g., 0.13 mole) and 4-benzyloxy-3-acetoxy-1-butene (21.0 g., 0.096 mole) containing benzoxyl peroxide (50 mg.) is stirred at room temperature for 20 hours. The reaction mixture is taken up in ether (200 ml.), washed with saturated sodium bicarbonate solution until neutral and then with brine and dried over sodium sulfate. The ether is removed in vacuo and the resulting oil is purified by chromatography over silica gel using hexane-ethyl acetate (80-20) to elute. From the proper fraction there is obtained 18.0 g. (64%) of the title compound as a heavy oil.

Workup

  1. washwashed with saturated sodium bicarbonate solution until neutral and then with brine
  2. dry with materialdried over sodium sulfate
  3. customThe ether is removed in vacuo
  4. customthe resulting oil is purified by chromatography over silica gel
  5. washto elute
  6. customFrom the proper fraction there is obtained 18.0 g

Sources & evidence

ORD record
ord-ae1412ceed724155a4c128471fe44c70
Source dataset
uspto-grants-1978_05
Patent number
US04087435

Reaction notes

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