Water → HCID 68773571, compound

HRID 1471368Notes

Reaction equation

HRID 1471368 reaction equation
O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:21][C@@H:22]1[CH:31]=[CH:30][CH2:29][C:24]2([CH2:28][CH2:27][CH2:26][CH2:25]2)[C@H:23]1[C:32](=[O:36])/[CH:33]=[CH:34]/[CH3:35]>C1C=CC=CC=1>[CH3:21][C@@H:22]1[CH:31]=[CH:30][CH2:29][C:24]2([CH2:28][CH2:27][CH2:26][CH2:25]2)[C@H:23]1[C:32](=[O:36])[CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 68771630HCID 68771630, compound

Product 1

HCID 68773571HCID 68773571, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

After argon bubbling, a mixture of benzene (70 ml) and water (0.15 ml) was treated with triphenylphosphine-cooper (I)-hydride hexamer (3.3 g, 1.68 mmol). The resulting mixture was stirred for five min., treated with a solution of (E)-1-(rel-(6S,7R)-7-methylspiro[4.5]dec-8-en-6-yl)but-2-en-1-one (2 g, 9.16 mmol) in benzene (10 ml) and stirred for 2 h at 20° C. The reaction mixture was then stirred for 30 min under air, filtered, and concentrated. FC (SiO2, hexane/MTBE 70:1) of the crude product (4.07 g) gave 1-(rel-(6S,7R)-7-methylspiro[4.5]dec-8-en-6-yl)butan-1-one (0.80 g, 40%). Boiling point: 100° C. (0.08 mbar).

Workup

  1. stirringstirred for 2 h at 20° C
  2. stirringThe reaction mixture was then stirred for 30 min under air
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d641b673866548ab8e724b535110bbb9
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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