Hydrochloric Acid → HCID 21707617, compound

HRID 1978255Notes

Reaction equation

HRID 1978255 reaction equation
[CH3:1][C:2]1([CH3:15])[C:6]([CH3:7])=[CH:5][CH2:4][CH:3]1[CH2:8][CH:9]1[CH2:11][CH:10]1[C:12](=[O:14])[CH3:13].[BH4-].[Na+].Cl>C(O)C>[CH3:15][C:2]1([CH3:1])[C:6]([CH3:7])=[CH:5][CH2:4][CH:3]1[CH2:8][CH:9]1[CH2:11][CH:10]1[CH:12]([OH:14])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 21707631HCID 21707631, compound

Product 1

HCID 21707617HCID 21707617, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.5 g (7.3 mmol) of 1-[2-(2,2,3-trimethylcyclopent-3-enylmethyl)cyclopropyl]ethanone dissolved in 5 ml of ethanol was added to a suspension of 0.50 g (13 mmol) of sodium borohydride in 30 ml of the same solvent under nitrogen at 5° C. The reaction mixture was stirred at room temperature for further 2 hours. After addition of 50 ml of 1N aqueous hydrochloric acid it was extracted with 200 ml of MTBE, the organic layer washed with 2×100 ml of brine, dried (MgSO4) evaporated in vacuo and bulb-to-bulb distilled to give 1.3 g of 1-[2-(2,2,3-trimethylcyclopent-3-enylmethyl)cyclopropyl]ethanol (87% yield).

Workup

  1. extractionwas extracted with 200 ml of MTBE
  2. washthe organic layer washed with 2×100 ml of brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo and bulb-to-bulb
  5. distillationdistilled

Sources & evidence

ORD record
ord-889cf5b5f45f41d7b42a00e949a59f9f
Source dataset
uspto-grants-2001_05
Patent number
US06235943B1

Reaction notes

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