Triphenylphosphine → HCID 66841610, compound

HRID 1929083Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH2:10][OH:11])[C:6]=2[CH:12]=1.[CH3:13][CH2:14][O:15][C:16]([C:18]1[N:19]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:20]2[C:25]([CH:26]=1)=[C:24](O)[CH:23]=[CH:22][CH:21]=2)=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(C(C)C)C(C)C)C>C1COCC1>[CH3:13][CH2:14][O:15][C:16]([C:18]1[N:19]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[C:20]2[C:25]([CH:26]=1)=[C:24]([O:11][CH2:10][C:7]1[C:6]3[CH:12]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:9][CH:8]=1)[CH:23]=[CH:22][CH:21]=2)=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

100 (4 g, 21.9 mmol), 102 (6.7 g, 21.9 mmol), triphenylphosphine (17.3 g, 65.8 mmol) and 40% diethyl azadicarboxylate solution (31.8 ml, 65.8 mmol) are dissolved in THF and cooled to 0° C. Then a solution of N-ethyldiisopropylamine (11.2 ml, 65.8 mmol) in THF is added dropwise. After the addition is completed, the mixture is stirred at room temperature for 2 h. Then the mixture is evaporated under reduced pressure. The residue is diluted with ethyl acetate, washed with saturated NaHCO3-solution and dried over Na2SO4. The crude product is purified by Flash-chromatography (ethyl acetate/hexanes (3:7), silicagel).

Workup

additionAfter the addition
customThen the mixture is evaporated under reduced pressure
additionThe residue is diluted with ethyl acetate
washwashed with saturated NaHCO3-solution
dry with materialdried over Na2SO4
customThe crude product is purified by Flash-chromatography (ethyl acetate/hexanes (3:7), silicagel)

Sources & evidence

ORD record: ord-072ed7d33d734ea1991b6a3cf903217c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183366B2

Reaction notes

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