3-Phenylcyclobutanone → Ethyl 2-(3-phenylcyclobutylidene)propanoate

HRID 1713906Notes

Reaction equation

HRID 1713906 reaction equation
C(O[C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20]CC[C:17](=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[C:27]1(C2CC(=O)C2)C=CC=CC=1>>[C:12]1([CH:15]2[CH2:16][C:17](=[C:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20]2)[CH:11]=[CH:10][CH:9]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 1429633-PhenylcyclobutanoneHCID 72292906Ethyl {3-[4-(benzyloxy)phenyl]cyclohexylidene}acetate2×

Product 1

HCID 59464266Ethyl 2-(3-phenylcyclobutylidene)propanoate

Procedure

Following the general procedure described for ethyl {3-[4-(benzyloxy)phenyl]cyclohexylidene}acetate (Intermediate 891i), replacing 3-[4-(benzyloxy)phenyl]cyclohexanone with 3-phenylcyclobutanone (J. Org. Chem., 2005, 70(11), 4549-4552) and triethyl phosphonoacetate with triethyl phosphonopropionate the title compound was obtained; 1H NMR δ (CDCl3): 1.24-1.32 (3H, m), 1.75-1.76 (3H, m), 2.87-2.91 (1H, m), 3.19-3.23 (2H, m), 3.54-3.59 (2H, m), 4.09-4.21 (2H, m), 7.19-7.36 (5H, m); MS m/e MH+ 231.

Sources & evidence

ORD record
ord-8b7a6b95512f4afa8843c97d16e40bf1
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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