Diketene → 2-[4-(2-Benzyloxyethoxy)phenyl]ethylacetoacetate

HRID 652532Notes

Reaction equation

HRID 652532 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.[CH2:21]=[C:22]1[O:26][C:24](=[O:25])[CH2:23]1>>[CH2:14]([O:13][CH2:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][O:1][C:24](=[O:25])[CH2:23][C:22]([CH3:21])=[O:26])=[CH:5][CH:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 12661DiketeneHCID 201975371-(2-Hydroxyethyl)-4-(2-benzyloxyethoxy)benzene

Product 1

HCID 1317147152-[4-(2-Benzyloxyethoxy)phenyl]ethylacetoacetate

Procedure

Diketene (3-buteno-β-lactone, available, e.g., from Aldrich Chemical Co.) is then added to the hydroxyalkylbenzene derivative 4 under basic conditions, e.g., using triethylamine in dimethoxyethane (DME) to form a ω-phenylalkylacetoacetate derivative (5). For example, 1-(2-hydroxyethyl)-4-(2-benzyloxyethoxy)benzene is reacted with diketene to afford 2-[4-(2-benzyloxyethoxy)phenyl]ethylacetoacetate (5) (Step 5).

Sources & evidence

ORD record
ord-88550f60f5f04a07943febe0240c039f
Source dataset
uspto-grants-1987_06
Patent number
US04672071

Reaction notes

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