Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 68641221, compound

HRID 1053985Notes

Reaction equation

HRID 1053985 reaction equation
[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:10]=1[CH2:11][N:12]1[C:16]([CH3:17])=[CH:15][C:14]([CH:18]=O)=[N:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][O:26][C:27]([CH:29]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:28]>C1COCC1.CCOC(C)=O>[CH3:25][O:26][C:27](=[O:28])/[CH:29]=[CH:18]/[C:14]1[CH:15]=[C:16]([CH3:17])[N:12]([CH2:11][C:10]2[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:13]=1

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 57875550HCID 57875550, compound

Product 1

HCID 68641221HCID 68641221, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of aldehyde 13, (1 g, 2.9 mmol) in THF was added (methoxycarbonylmethylene)triphenylphosphorane, 2 g (6 mmol). The mixture was stirred at room temperature for 70 hours. The mixture was diluted with EtOAc and the organic phase was washed with 2M HCl, saturated NaHCO3 and brine, dried over MgSO4 and evaporated in vacuo. The crude unsaturated ester 14 was purified on silica to yield 1.2 g as a white solid (99%).

Workup

  1. washthe organic phase was washed with 2M HCl, saturated NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe crude unsaturated ester 14 was purified on silica

Sources & evidence

ORD record
ord-72d51d6f4f364d69b3edb6ecbcce2f17
Source dataset
uspto-grants-2016_07
Patent number
US09394284B2

Reaction notes

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