Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 67740254, compound

HRID 580992Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH:10]=O)[CH:7]=[CH:6][C:5]=1[C:12]#[C:13][C:14]1([OH:22])[CH:19]2[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]2)[CH2:15]1)[CH3:2].[C:23]([CH:28]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:25][CH2:26][CH3:27])=[O:24]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH:10]=[CH:28][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]=[CH:6][C:5]=1[C:12]#[C:13][C:14]1([OH:22])[CH:19]2[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]2)[CH2:15]1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-[2-(2-ethoxy-4-formylphenyl)ethynyl]quinuclidin-3-ol (598 mg), carbethoxymethylenetriphenylphosphorane (1.04 g) in toluene (10 ml) was heated at 100° C. for 5 hours. The reaction mixture was cooled to ambient temperature and the toluene evaporated to give a solid which was crystallised from acetonitrile to give 3-[2-(2-ethoxy-4-(2-ethoxycarbonylethenyl)phenyl)ethynyl]quinuclidin-3-ol (328 mg) as a solid, m.p. 152-153° C.; microanalysis found: C, 71.5; H, 7.3; N, 3.7%; C22H27NO4 requires: C, 71.5: H, 7.37; N, 3.79%; NMR (CDCl3): 1.33(3H, t), 1.36-1.52(4H, m), 1.55-1.70(1H, m), 1.90-2.30(4H, m), 2.73-3.00(4H, m), 3.04(1H, d), 3.34(1H, dd), 4.09(2H, q), 4.26(2H, q), 6.33-6.45(1H, d), 6.93-7.03(1H, d,), 7.03(1H, dd), 7.35(1H, d), 7.60(1H, d); m/Z 370 (M+H).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
customthe toluene evaporated
customto give a solid which
customwas crystallised from acetonitrile

Sources & evidence

ORD record: ord-7888f1c486d941d68fe78f181fcafd8e
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05919793

Reaction notes

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