Water → HCID 86608638, compound

HRID 2097311Notes

Reaction equation

HRID 2097311 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16](=[O:37])[CH:17]=[P:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.Cl[C:46](=[O:52])[C:47]([O:49][CH2:50][CH3:51])=[O:48].O>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16](=[O:37])[C:17](=[P:18]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:46](=[O:52])[C:47]([O:49][CH2:50][CH3:51])=[O:48])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 86608637HCID 86608637, compound

Product 1

HCID 86608638HCID 86608638, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Procedure

To a solution of 1-(2-Benzyloxy-5-chloro-phenyl)-2-(triphenyl-λ5-phosphanylidene)-ethanone (0.49 g, 0.94 mmol), NEt3 (96 mg, 0.94 mmol) and DMAP (12 mg, 0.09 mmol) in dry toluene (20 ml) at room temperature, ethyl chlorooxoacetate (0.38 g, 2.78 mmol) in toluene (5 ml) was added. The mixture was stirred for 2 hours and poured into water (50 ml). The organic layer was separated and the aq. layer was extracted with EtOAc (2×40 ml). The combined organic layers were then washed with sat. NaHCO3 solution (2×40 ml), sat. citric acid (1×40 ml), brine (1×40 ml) and dried. Crude oil (0.36 g) was purified by chromatography, eluted with EtOAc. Rf=0.88. 1H NMR (d6-acetone) δ=7.75-7.40 (15H, m); 7.30 (1H, dd); 7.15 (1H, d); 7.05 (1H, d); 5.10 (2H, s); 3.60 (2H, q) and 1.10 (3H, s). LCMS: (M+1)+=621.2 (RT=6.49 min.)

Workup

  1. customThe organic layer was separated
  2. extractionthe aq. layer was extracted with EtOAc (2×40 ml)
  3. washThe combined organic layers were then washed with sat. NaHCO3 solution (2×40 ml), sat. citric acid (1×40 ml), brine (1×40 ml)
  4. customdried
  5. customCrude oil (0.36 g) was purified by chromatography
  6. washeluted with EtOAc

Sources & evidence

ORD record
ord-f8d308bf9ade448db6886df56ef13599
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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