Water → HCID 59714837, compound

HRID 2223868Notes

Reaction equation

HRID 2223868 reaction equation
[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][C:29]([CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])([C:34](OC)=[O:35])[C:30](OC)=[O:31])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][C:29]([CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])([CH2:34][OH:35])[CH2:30][OH:31])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si:2]([C:15]([CH3:16])([CH3:18])[CH3:17])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59715035HCID 59715035, compound

Product 1

HCID 59714837HCID 59714837, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of dimethyl 2-[2-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]ethyl]-2-pent-4-enylmalonate (910 mg) in diethyl ether (15 mL) was added lithium aluminum hydride (117 mg) under ice cooling. After stirring the solution at room temperature for 1 hour, water (0.12 mL) and a 15% aqueous sodium hydroxide solution (0.12 mL) were successively added thereto. The solution was stirred at room temperature for 15 minutes. Water (0.36 mL) was then added and the solution was stirred at room temperature for additional 15 minutes. The solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=6:4) to give the title compound (640 mg).

Workup

  1. stirringThe solution was stirred at room temperature for 15 minutes
  2. stirringthe solution was stirred at room temperature for additional 15 minutes
  3. dry with materialThe solution was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-9e217166a1214ddb812062476fa48bed
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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