Triphenylphosphine → HCID 67972521, compound

HRID 1911825Notes

Reaction equation

HRID 1911825 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C@H:28]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:13][CH2:14][CH:15]1[O:17][CH:16]1[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C@H:28]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:13][CH2:14][C:15](=[O:17])[CH2:16][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][CH:27]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86666746HCID 86666746, compound

Product 1

HCID 67972521HCID 67972521, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the title compound from Step F above (1.00 g, 1.69 mmol) and palladium acetate Pd(OAc)2 (0.064 g, 0.28 mmol) in ethanol (15 ml) was degassed and flushed with N2, and then triphenylphosphine (0.298 g, 1.137 mmol) was added. The reaction mixture was refluxed overnight. After removal of the solvent, the residue was purified by column chromatography (0-20% then 20% ethyl acetate in hexanes). 0.50 g (50%) of the title compound was obtained. 1H NMR (CDCl3, 400 MHz): δ8.14 (d, J=8.6 Hz, 2H), 7.53-7.28 (m, 12H), 5.13 (s, 2H), 4.97 (d, J=9.4 Hz, 1H), 4.86 (s, 1H), 4.06 (s, 3H), 3.85 (s, 2H), 2.77-2.64 (m, 2H), 2.07 (m, 1H), 1.85-1.79 (m, 2H), 1.05 (s, 9H), 0.19 (s, 3H), 0.00 (s, 3H). MS: m/z (ESI) 590 (M+1).

Workup

  1. customwas degassed
  2. customflushed with N2
  3. temperatureThe reaction mixture was refluxed overnight
  4. customAfter removal of the solvent
  5. customthe residue was purified by column chromatography (0-20%

Sources & evidence

ORD record
ord-c2ad2a31f6914e0b846a2431d6fd2b2b
Source dataset
uspto-grants-2013_12
Patent number
US08604038B2

Reaction notes

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