Sodium hydride → HCID 23371323, compound

HRID 1899784Notes

Reaction equation

HRID 1899784 reaction equation
[CH3:1][O:2]/[C:3](/[C:9]1[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=1[CH2:11]P(=O)(OC)OC)=[CH:4]/[C:5]([O:7][CH3:8])=[O:6].[CH2:22]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[H-].[Na+].[NH4+].[Cl-]>CN(C)C=O>[CH2:22]([O:29][C:30]1[CH:31]=[CH:32][C:33]([CH:34]=[CH:11][C:10]2[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=2/[C:3](/[O:2][CH3:1])=[CH:4]\[C:5]([O:7][CH3:8])=[O:6])=[CH:36][CH:37]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 20153620HCID 20153620, compound

Product 1

HCID 23371323HCID 23371323, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3.0 g (10 mmol) of dimethyl (E)-2-(1-methoxy-2-methoxycarbonylethenyl)benzylphosphonate and 2.1 g (10 mmol) of 4-benzyloxybenzaldehyde in 50 ml of dimethylformamide is added dropwise at room temperature to 0.26 g (11 mmol) of NaH in 20 ml of dimethylformamide. The mixture is stirred for 3 h, and then NH4Cl solution is added. After extraction with ethyl acetate, the organic phase is washed with water, dried over Na2SO4 and concentrated. Recrystallization from diisopropyl ether/n-hexane results in 1.9 g (48%) of pale yellow crystals of methyl 2-[2-(4-benzyloxyphenyl)-(E)-ethenyl]-(E)-β-methoxycinnamate of melting point 118°-120° C.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washthe organic phase is washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customRecrystallization from diisopropyl ether/n-hexane

Sources & evidence

ORD record
ord-75b8d5ee470b4750908cb2475ca41f07
Source dataset
uspto-grants-1996_11
Patent number
US05573999

Reaction notes

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