Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 70359873, compound

HRID 1651664Notes

Reaction equation

HRID 1651664 reaction equation
[O:1]([CH2:9][C@H:10]1[C:15](=O)[CH2:14][O:13][C@@H:12]([CH3:17])[O:11]1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[C:18]([CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:20][CH2:21][CH3:22])=[O:19]>O1CCCC1>[O:1]([CH2:9][C@H:10]1[C:15](=[CH:23][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][O:13][C@@H:12]([CH3:17])[O:11]1)[Si:2]([C:5]([CH3:6])([CH3:7])[CH3:8])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 14134382HCID 14134382, compound

Product 1

HCID 70359873HCID 70359873, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2R,4S)-4-t-butyldimethylsiloxymethyl -2-methyl-1,3-dioxan-5-one (2.50 g) and carboethoxymethylenetriphenylphosphorane (4.00 g) in tetrahydrofuran (25 ml) was stirred at room temperature for 24 hours and the solvent was evaporated in vacuo. The residue was chromatographed on a silica gel column (50 g) with a mixture of n-hexane and ethyl acetate (10:1) as an eluent to give (2R,4R)-4-t-butyldimethylsiloxymethyl-5-ethoxycarbonylmethylene-2-methyl-1,3-dioxane (2.09 g) as an oil.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was chromatographed on a silica gel column (50 g) with a mixture of n-hexane and ethyl acetate (10:1) as an eluent

Sources & evidence

ORD record
ord-87bbcc7c5f084265bdd4670381b6feb1
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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