Water → HCID 67621687, compound

HRID 322885Notes

Reaction equation

HRID 322885 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH3:15])=[O:13])(OCC)=O)C.[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH:46]=O)=[C:28]([CH:45]=1)[O:29][CH:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[CH3:44])[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>O1CCCC1>[CH3:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[CH:30]([O:29][C:28]1[CH:45]=[C:24]([O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:25]=[CH:26][C:27]=1/[CH:46]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 23204236HCID 23204236, compound

Product 1

HCID 67621687HCID 67621687, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension of sodium hydride (0.272 g; 60% w/v dispersion in mineral oil; 6.8 mmol) in tetrahydrofuran (100 mL) at 0° C. under nitrogen is treated, dropwise, with methyl (diethylphosphono)acetate (1.43 g) and stirred for 15 minutes. It is then treated with a solution of ethyl (RS)-4-(5-benzyloxy-2-formylphenoxy)-4-(2-methylphenyl)butanoate (1.96 g) in tetrahydrofuran (5 mL) in one portion, and the reaction mixture is stirred at ambient temperature for 15 minutes. The mixture is treated with water (100 mL) and extracted with ethyl acetate (3×100 mL), and the combined organic extracts are washed with brine (50 mL), dried over magnesium sulphate, and filtered and the solvent is removed in vacuo, to give ethyl (E)-(RS)-4-(2-methylphenyl)-4-[2-(2-methoxycarbonylethenyl)-5-benzyloxyphenoxy]butanoate, in the form of a yellow oil.

Workup

  1. additionis treated
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washthe combined organic extracts are washed with brine (50 mL)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-c05ca4ec8d994f02bc7e7a0f39972728
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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