Aluminium lithium hydride → 1-Hexanol, 3-mercapto-3-methyl-, (3S)-

HRID 393120Notes

Reaction equation

HRID 393120 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C@:8]([S:29]C([C@@]12C(C)(C)C(C)(CC1)C(=O)O2)=O)([CH2:26][CH2:27][CH3:28])[CH2:9][CH2:10][O:11]C(=O)C1C=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1>CCOCC.C1COCC1>[SH:29][C@@:8]([CH3:7])([CH2:26][CH2:27][CH3:28])[CH2:9][CH2:10][OH:11]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 88048471HCID 88048471, compound

Product 1

HCID 101977701-Hexanol, 3-mercapto-3-methyl-, (3S)-Yield 27.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.28 g (7.5 mmol) of LiAlH4 in 10 ml of Et2O was added a solution of 1.3 g of (1S,3S)-3,5-dinitro-benzoic acid 3-methyl-3-(4,7,7-trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carbonylsulfanyl)-hexyl ester of step (b) in 10 ml of THF. The reaction mixture was stirred at room temperature overnight, quenched with 20 ml of water and filtered over Celite. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was distilled (bulb to bulb, 0.06 Torr, up to 190° C.) and gave 100 mg (27%) of (S)-3-mercapto-3-methyl-hexan-1-ol in form of a colorless oil.

Workup

  1. customquenched with 20 ml of water
  2. filtrationfiltered over Celite
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. distillationThe residue was distilled (bulb to bulb, 0.06 Torr

Sources & evidence

ORD record
ord-58fd75287ce740068235fbbdf569b38b
Source dataset
uspto-grants-2004_10
Patent number
US06805893B2

Reaction notes

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