HCID 19378100, compound → HCID 19378071, compound

HRID 2211017Notes

Reaction equation

HRID 2211017 reaction equation
[SH:1][C:2]([CH:5]1[O:10][C:8](=[O:9])[CH:7]([CH2:11][SH:12])[CH2:6]1)([CH3:4])[CH3:3]>C(Cl)Cl.C(Br)C=C.CCOCC>[CH2:4]([S:1][C:2]([CH:5]1[O:10][C:8](=[O:9])[CH:7]([CH2:11][S:12][CH2:7][CH:6]=[CH2:5])[CH2:6]1)([CH3:4])[CH3:3])[CH:2]=[CH2:3]

Participants

5

Reactant 1

HCID 19378100HCID 19378100, compound

Product 1

HCID 19378071HCID 19378071, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 7841Allyl bromideSolvent

Procedure

To a solution of 4-(1-mercapto-1-methylethyl)-2-mercaptomethyl-4-butanolide (0.24 g) in methylene chloride (3 ml), allyl bromide (1.0 ml) and N,N-(diisopropyl)ethylamine (1.0 ml) were added under nitrogen atmosphere. The mixture was stirred overnight at room temperature. The mixture was diluted with ether (50 ml) and washed with 2N hydrochloric acid and saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 0.142 g (43%) of cis-form (compound No.12-1) and 0.170 g (51%) of transform (compound No.12-2) of the titled compound.

Workup

  1. washwashed with 2N hydrochloric acid and saturated sodium chloride solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe oily residue was purified by silica gel column chromatography
  5. customto give 0.142 g (43%) of cis-form (compound No.12-1) and 0.170 g (51%)

Sources & evidence

ORD record
ord-db584e54c3a94e1195a26356a8ac06f4
Source dataset
uspto-grants-1995_10
Patent number
US05461158

Reaction notes

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