Ammonia → HCID 68153783, compound

HRID 2039375Notes

Reaction equation

HRID 2039375 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([Si:10]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[O:11][CH:12]1[CH2:17][CH2:16][CH:15](C(C)C(OCC)=O)[CH2:14][CH2:13]1)([CH3:9])[CH3:8].C(OCC)(=O)C.N.[CH2:38]1C[O:41][CH2:40][CH2:39]1>>[CH:28]([Si:10]([CH:25]([CH3:27])[CH3:26])([CH:7]([CH3:9])[CH3:8])[O:11][CH:12]1[CH2:13][CH2:14][CH:15]([CH:40]([OH:41])[CH2:39][CH3:38])[CH2:16][CH2:17]1)([CH3:30])[CH3:29]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 68153770HCID 68153770, compound

Product 1

HCID 68153783HCID 68153783, compound

Procedure

Lithium aluminum hydride (2.7 g) was suspended in THF (200 ml). Ethyl 4-triisopropylsilyloxycyclohexylpropionate (s40) (21.3 g) was added dropwise to the suspension in the temperature range of −20° C. to −10° C., and the mixture was stirred at the same temperature range for 2 hours. After the completion of reaction had been confirmed by means of GC analysis, ethyl acetate and a saturated aqueous solution of ammonia were added successively to the reaction mixture under ice-cooling, and the deposits were removed by filtration through Celite. The filtrate was extracted with ethyl acetate. The combined organic layers were washed successively with water and brine, and dried over anhydrous magnesium sulfate. Distillation of the solvent under reduced pressure gave 4-triisopropylsilyloxycyclohexyl propanol (s41) (18.3 g). The yield based on the compound (s40) was 97.40.

Workup

  1. customAfter the completion of reaction
  2. temperaturecooling
  3. customthe deposits were removed by filtration through Celite
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washThe combined organic layers were washed successively with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationDistillation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-9da5aa6fd5284ee3bd850559c48f3cd4
Source dataset
uspto-grants-2013_11
Patent number
US08580146B2

Reaction notes

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