Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 131717466, compound

HRID 654319Notes

Reaction equation

HRID 654319 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][CH:19]([CH3:21])[CH3:20])[C@H:10]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O=[O+][O-].C1(P(=C[C:45]([O:47][CH3:48])=[O:46])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][CH:19]([CH3:21])[CH3:20])[C@H:10]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])/[CH:11]=[CH:12]/[C:45]([O:47][CH3:48])=[O:46])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 24823OzoneHCID 57068580HCID 57068580, compound

Product 1

HCID 131717466HCID 131717466, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.22 g (0.69 mmol) of the resultant compound of Example 32 in 15 ml of dichloromethane was cooled to -78° C. and treated with a stream of O3 in air until the blue color persisted. The solution was subsequently purged with air until the blue color was discharged, treated with 0.5 ml of dimethylsulfide, allowed to warm to ambient temperature over 40 min, and treated with 0.29 g (0.87 mmol) of methyl (triphenylphosphoranylidene)acetate. The resulting solution was stirred at ambient temperature for 4 h, concentrated in vacuo, partitioned between dichloromethane and water, dried over MgSO4, and concentrated. Silica gel chromatography using 30% ethyl acetate in hexane provided 0.08 g (31%) of the desired compound (Rf 0.17, 30% ethyl acetate in hexane). 1H NMR (CDCl3) δ 0.89 (d, J=7 Hz, 3 H), 0.93 (d, J=7 Hz, 3 H), 1.22 (m, 2 H), 1.44 (s, 9 H), 1.69 (m, 1 H), 3.06 (s, 3 H), 3.78 (s, 3 H), 3.92 (m, 1 H), 4.58 (br d, 1 H), 5.40 (m, 1 H), 6.16 (dd, J=15, 2 Hz, 1 H), 6.87 (dd, J=15, 6 Hz, 1 H). Mass spectrum: (M+H)+ =380.

Workup

  1. customThe solution was subsequently purged with air until the blue color
  2. additiontreated with 0.5 ml of dimethylsulfide
  3. concentrationconcentrated in vacuo
  4. custompartitioned between dichloromethane and water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5e3cf0d2b6ca4488870b0d4e26b76463
Source dataset
uspto-grants-1992_07
Patent number
US05130468

Reaction notes

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