Hexane → (E)-ethyl 3-cyclopentylacrylate

HRID 2103604Notes

Reaction equation

HRID 2103604 reaction equation
C(P([CH2:8][C:9]([O-:11])=[O:10])(CC)CC)C.[CH3:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[H-].[Na+].[CH:20]1(C=O)CCC[CH2:21]1>C1COCC1>[CH2:20]([O:11][C:9](=[O:10])/[CH:8]=[CH:12]/[CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH3:21]

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 70106CyclopentanecarbaldehydeHCID 178477249HCID 178477249, compound

Product 1

HCID 11182849(E)-ethyl 3-cyclopentylacrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Following the method of example 54a, reaction of triethylphosphinoacetate (196 g, 870 mmol) with hexane-washed sodium hydride (60% in mineral oil, 35 g, 870 mmol) in THF (1200 ml) and cyclopentanecarbaldehyde (86 g, 870 mmol) in THF (300 ml) gives the title product as an oil (59.1 g). MS (m/e): 169.1 (M+H).

Sources & evidence

ORD record
ord-0e2300ffdb7a4af29add24656ea50933
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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