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

HRID 397245Notes

Reaction equation

HRID 397245 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-b43b6d4874bb4cac8760e7ffda129e3a
Source dataset
uspto-grants-2003_08
Patent number
US06610346B1

Reaction notes

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