Pentanal → HCID 11636872, compound

HRID 1784132Notes

Reaction equation

HRID 1784132 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[CH:7](=[O:12])[CH2:8][CH2:9][CH2:10][CH3:11].C(P(CCCC)CCCC)CCC>C1COCC1>[OH:12][CH:7]([C:2]1[C:1](=[O:6])[CH2:5][CH2:4][CH:3]=1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8063PentanalHCID 135882-Cyclopenten-1-oneHCID 13831Tributylphosphine

Product 1

HCID 11636872HCID 11636872, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclopentenone (1.23 g, 15 mmol), pentanal (1.94 g, 22.5 mmol), rac-1,1′-bi-2-naphthol (429 mg, 1.5 mmol) and tributyl phosphine (606 mg, 3 mmol) in dry THF (12 ml) was stirred at 20° C. under Argon for 3 hours. The solution was then passed through a short column of SiO2 (cyclohexane/Et2O 6:4) to obtain the pure title compound in 92% yield.

Sources & evidence

ORD record
ord-3f464347dcc84cd7a0f1603cd8663c97
Source dataset
uspto-grants-2009_03
Patent number
US07501539B2

Reaction notes

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