Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 59180245, compound

HRID 601942Notes

Reaction equation

HRID 601942 reaction equation
[Cl:1][C:2]1[CH2:7][CH:6]2[CH:4]([CH2:5]2)[C:3]=1[CH:8]=O.[CH2:10]([O:12][C:13]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:14])[CH3:11]>>[Cl:1][C:2]1[CH2:7][C@H:6]2[C@H:4]([CH2:5]2)[C:3]=1/[CH:8]=[CH:15]/[C:13]([O:12][CH2:10][CH3:11])=[O:14]

Participants

3

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 72536511HCID 72536511, compound

Product 1

HCID 59180245HCID 59180245, compound

Procedure

3-Chlorobicyclo[3.1.0]hex-2-ene-2-carbaldehyde (142 mg, 0.67 mmol) was olefinated according to General Procedure 1.1.B with ethoxycarbonylmethylene triphenylphosphorane ((487 mg, 1.4 mmol). The material was purified by chromatography, eluting with heptane-EtOAc, gradient 0 to 10% EtOAc to afford the title compound. 142 mg. 1H NMR (CHLOROFORM-d) δ: 7.57 (d, J=15.8 Hz, 1H), 6.11 (d, J=15.7 Hz, 1H), 4.25 (q, J=7.1 Hz, 2H), 3.01 (dd, J=19.1, 7.3 Hz, 1H), 2.65 (dd, J=19.1, 2.9 Hz, 1H), 1.93-2.03 (m, 1H), 1.61 (qd, J=7.3, 4.3 Hz, 1H), 1.33 (t, J=7.1 Hz, 3H), 1.00 (td, J=7.5, 4.7 Hz, 1H), 0.13-0.21 (m, 1H).

Workup

  1. customThe material was purified by chromatography
  2. washeluting with heptane-EtOAc, gradient 0 to 10% EtOAc

Sources & evidence

ORD record
ord-8254a0bedc784a4e99360ee85cea34e7
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…