Water → Triphenylphosphine

HRID 1357494Notes

Reaction equation

HRID 1357494 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH2:20].C([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])C.[CH2:28]1[CH2:32][O:31][CH2:30][CH2:29]1>>[CH2:2]([C@@H:25]1[C@@H:24]2[C@@H:26]([NH:23]2)[CH:27]=[C:29]([C:30]([O:31][CH3:32])=[O:20])[CH2:28]1)[CH:1]=[CH2:6].[CH:17]1[CH:16]=[CH:15][C:14]([P:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11776Triphenylphosphine

Product 2

HCID 11776TriphenylphosphineHCID 86759064HCID 86759064, compound

Procedure

Triphenylphosphine (1.14 g, 4.35 mmol) was slowly added to a room temperature solution of Example 1K (0.80 g, 2.54 mmol) in THF (30 mL). After stirring for 2 hours, water (3.0 mL) and triethylamine (1.0 mL, 7.19 mmol) were added. The mixture was stirred for 10 hours, and concentrated. The concentrate was chromatographed on silica gel using ethyl acetate to afford the desired product with Ph3P as a contaminant.

Workup

  1. stirringThe mixture was stirred for 10 hours
  2. concentrationconcentrated
  3. customThe concentrate was chromatographed on silica gel

Sources & evidence

ORD record
ord-0a6d15e7b9384824a0bc601f69778db9
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

Loading…