Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 86638801, compound

HRID 601948Notes

Reaction equation

HRID 601948 reaction equation
[Cl:1][C:2]1[CH2:7][C@H:6]2[C@H:4]([C@H:5]2[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]=1[CH:16]=O.[CH2:18]([O:20][C:21]([CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:22])[CH3:19]>>[Cl:1][C:2]1[CH2:7][C@H:6]2[C@H:4]([C@H:5]2[CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:3]=1/[CH:16]=[CH:23]/[C:21]([O:20][CH2:18][CH3:19])=[O:22]

Participants

3

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 86638802HCID 86638802, compound

Product 1

HCID 86638801HCID 86638801, compound

Procedure

±(1S,5R,6S)-3-chloro-6-phenethylbicyclo[3.1.0]hex-2-ene-2-carbaldehyde (11 mmol crude weight) was olefinated with ethoxycarbonylmethylene triphenylphosphorane (4.6 g, 13.2 mmol) according to General Procedure 1.1.B to afford the title compound. The material was purified by chromatography, eluting with heptane-EtOAc, gradient 0 to 10% EtOAc. 2.2 g. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.08-1.19 (m, 1H), 1.23-1.31 (m, 1H), 1.30-1.37 (m, 3H), 1.39-1.51 (m, 1H), 1.59-1.68 (m, 1H), 2.14 (td, J=7.25, 3.03 Hz, 1H), 2.38 (dd, J=19.57, 2.68 Hz, 1H), 2.53-2.66 (m, 2H), 2.92 (dd, J=19.55, 7.88 Hz, 1H), 4.20-4.31 (m, 2H), 6.04 (d, J=15.72 Hz, 1H), 7.10-7.22 (m, 3H), 7.23-7.31 (m, 2H), 7.61 (d, J=15.72 Hz, 1H).

Sources & evidence

ORD record
ord-2c305e605ad54a80bc9bfabe90c8564b
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…