Diisobutylaluminum hydride → HCID 54232710, compound

HRID 2352660Notes

Reaction equation

HRID 2352660 reaction equation
[CH2:1]([S:7][CH:8]=[CH:9][C:10](OC)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CC(C[AlH]CC(C)C)C>CCCCCC>[CH2:1]([S:7][CH:8]=[CH:9][CH2:10][OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 53796704HCID 53796704, compound

Product 1

HCID 54232710HCID 54232710, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a cooled (5°) solution of the above methyl 3-(hexylthio)-2-propenoate (0.84 g, 4.2 mmol) in 5 ml of hexane is added dropwise 10.7 ml (9.7 mmol) of a DIBAL solution (0.91 M/hexane). After addition is complete, the ice bath is removed. Aqueous methanol (3 ml MeOH:2 ml H2O) is added dropwise, followed by ether, and the reaction mixture is filtered, washed with ether and then stripped of solvent to give 3-hexylthio-2-propenol.

Workup

  1. additionAfter addition
  2. customthe ice bath is removed
  3. additionAqueous methanol (3 ml MeOH:2 ml H2O) is added dropwise
  4. filtrationthe reaction mixture is filtered
  5. washwashed with ether

Sources & evidence

ORD record
ord-5629791f11a240b8bc3ec412dd879560
Source dataset
uspto-grants-1989_10
Patent number
US04877899

Reaction notes

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