Triphenylphosphine → HCID 54347543, compound

HRID 1253341Notes

Reaction equation

HRID 1253341 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClCl.[CH2:22]([O:29][C:30]([NH:32][C:33]1[S:34][CH:35]=[C:36]([C:38](=[C:42](Cl)[CH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[O:47])[C:39]([OH:41])=[O:40])[N:37]=1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:22]([O:29][C:30]([NH:32][C:33]1[S:34][CH:35]=[C:36]([C:38](=[CH:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)=[O:47])[C:39]([OH:41])=[O:40])[N:37]=1)=[O:31])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 24526ChlorineHCID 53884697HCID 53884697, compound

Product 1

HCID 54347543HCID 54347543, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of triphenylphosphine (284 mg) in tetrahydrofuran (4 ml) cooled at -15° C. are added a 0.85M solution of chlorine in carbon tetrachloride (1.27 ml), triethylamine (0.152 ml), and a solution of ketodiester (4) (160 mg) in tetrahydrofuran (2 ml). The mixture is warmed to room temperature, stirred for 6.5 hours, subjected to usual work-up, and silica gel chromatography to give chlorodiester (5). Yield: 67%.

Sources & evidence

ORD record
ord-e162158d000b42a7b65c7d14c9d71867
Source dataset
uspto-grants-1988_05
Patent number
US04748170

Reaction notes

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