Water → HCID 53863301, compound

HRID 1978265Notes

Reaction equation

HRID 1978265 reaction equation
[BH4-].[Na+].[Cl-].[Cl-].[Cl-].[Ce+3].[CH3:7][C:8](=[CH:12][CH2:13][CH:14]1[CH2:19][CH:18]2[C:16]([CH3:20])([CH2:17]2)[C:15]1([CH3:22])[CH3:21])[C:9](=[O:11])[CH3:10].O>CO>[CH3:7][C:8](=[CH:12][CH2:13][CH:14]1[CH2:19][CH:18]2[C:16]([CH3:20])([CH2:17]2)[C:15]1([CH3:21])[CH3:22])[CH:9]([OH:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 53673391HCID 53673391, compound

Product 1

HCID 53863301HCID 53863301, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.37 g (10 mmol) of sodium borohydride was added portionwise with cooling to the solution of 3.7 g (10 mmol) of cerium trichloride and 2.0 g (10 mmol) of 3-methyl-5-(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)pent-3-en-2-one in 25 ml of methanol. After 5 more minutes water was added and the mixture extracted with diethyl ether, dried (MgSO4) and evaporated in vacuo. Purification by flash chromatography on silica gel (eluent: hexane/MTBE 9:1) gave 1.3 g (58% yield) of 3-methyl-5-(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)pent-3-en-2-ol.

Workup

  1. extractionthe mixture extracted with diethyl ether
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. customPurification by flash chromatography on silica gel (eluent: hexane/MTBE 9:1)

Sources & evidence

ORD record
ord-250f707f96ec4702b1a64b0ca7fc3132
Source dataset
uspto-grants-2001_05
Patent number
US06235943B1

Reaction notes

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