1,2-Dimethoxyethane → 2-(Benzyloxyphenyl)ethylacetoacetate

HRID 652543Notes

Reaction equation

HRID 652543 reaction equation
C(OC(N[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1)=O)(C)(C)C.[CH2:18]=[C:19]1[O:23][C:21](=[O:22])[CH2:20]1.[CH2:24]([CH2:27]OC)[O:25]C>C(N(CC)CC)C>[CH2:24]([O:25][C:11]1[CH:10]=[CH:9][CH:14]=[CH:13][C:12]=1[CH2:15][CH2:16][O:17][C:21](=[O:22])[CH2:20][C:19]([CH3:18])=[O:23])[C:27]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 12661DiketeneHCID 11413715N-Boc-2-(4-aminophenyl)ethanol

Product 1

HCID 1317147162-(Benzyloxyphenyl)ethylacetoacetate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

A solution of 4.9 g of 1-benzyloxy-4-(2-hydroxyethyl)benzene (8) in 100 mL of dimethoxyethane (DME) and 5 drops triethylamine was heated to reflux and 1.8 mL of diketene was slowly added. The solvent was removed under reduced pressure to yield 6.4 g of 2-(benzyloxyphenyl)ethylacetoacetate (9), m.p. 54°-56° C.

Workup

  1. temperatureto reflux
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fca7c66d172340d7893718d26ba6eab6
Source dataset
uspto-grants-1987_06
Patent number
US04672071

Reaction notes

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