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

HRID 536565Notes

Reaction equation

HRID 536565 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-9e03df2a526c449db0015fd38b769bd7
Source dataset
uspto-grants-2014_10
Patent number
US08859606B2

Reaction notes

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