Triphenylphosphine → HCID 70446273, compound

HRID 246906Notes

Reaction equation

HRID 246906 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:32]([O:35][C:36]1[CH:37]=[C:38](O)[CH:39]=[CH:40][CH:41]=1)[CH:33]=[CH2:34].[CH3:43][O:44][C:45]1[CH:46]=[C:47]([CH:52]=[CH:53][C:54]=1[O:55][CH3:56])[CH:48]=[CH:49][CH2:50][OH:51]>C1COCC1.C(OCC)C>[CH2:32]([O:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:41]=1[O:51][CH2:50][CH:49]=[CH:48][C:47]1[CH:52]=[CH:53][C:54]([O:55][CH3:56])=[C:45]([O:44][CH3:43])[CH:46]=1)[CH:33]=[CH2:34]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3627113-(3,4-Dimethoxyphenyl)prop-2-en-1-olHCID 53141523-(Allyloxy)phenol

Product 1

HCID 70446273HCID 70446273, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (26.1 g, 0.15 mol) and triphenyl phosphine (39.3 g, 0.15 mol) were added to a solution of 3-allyloxyphenol (15 g, 0.1 mol) and 3,4-dimethoxycinnamyl alcohol (19.4 g, 0.1 mol) in THF (100 ml). The mixture was stirred at room temperature overnight, and ethyl ether was added. The precipitate was filtered off, and the filtrate was evaporated to a residue, which was purified by HPLC using hexane-ethyl acetate (4:1 v/v) as a liquid phase. 3,4-Dimethoxycinnamyl allyloxyphenyl ether was isolated as a crystalline mass (7.4 g, 23%), m.p. 60°-60.5° C.; NMR (CDCl3): δ3.93, 3.94 (s, s, 2 OCH3), 4.57 (d, t, J=5.5, 1.5, 1.5 Hz, CH2CH=CH2), 4.71 (d, d, J=6.0, 1.5 Hz, CH=CHCH2), 5.28-5.50 (m, CH2CH=CH2), 6.10 (m, CH2CH=CH2 ), 6.26-6.40 (m, CH=CHCH2), 6.56-7.28 (m, ArH).

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe filtrate was evaporated to a residue, which
  3. customwas purified by HPLC

Sources & evidence

ORD record
ord-ff9d07b89b0e49219a15a5da3d5d6512
Source dataset
uspto-grants-1987_11
Patent number
US04704462

Reaction notes

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