Toluene → Ethyl (naphtho[1,2-b]furan-3-yl)acetate

HRID 1768022Notes

Reaction equation

HRID 1768022 reaction equation
[O:1]1[CH2:5][C:4](=O)[C:3]2[CH:7]=[CH:8][C:9]3[C:14]([C:2]1=2)=[CH:13][CH:12]=[CH:11][CH:10]=3.[C:15]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:17])=[O:16].[C:38]1(C)C=CC=C[CH:39]=1>>[CH2:38]([O:17][C:15](=[O:16])[CH2:18][C:4]1[C:3]2[CH:7]=[CH:8][C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:2]=2[O:1][CH:5]=1)[CH3:39]

Participants

4

Reactant 3

HCID 1140TolueneHCID 1471593naphtho[1,2-b]furan-3(2H)-oneHCID 10870911Carboxymethylene triphenylphosphorane

Product 1

HCID 69455062Ethyl (naphtho[1,2-b]furan-3-yl)acetate

Procedure

A mixture of naphtho[1,2-b]furan-3 (2H)-one (1.85 g, 10 mmol) and (carboxymethylene)triphenylphosphorane (5.22 g, 15 mmol) was refluxed in toluene (100 ml) for 48 hrs. At the end, reaction mixture was concentrated and loaded over a silica-gel column. The column was eluted with hexane (500 ml) and later with 25% ethyl acetate. The product, naphtho[1,2-b]furan-3-yl-acetic acid ethyl ester was obtained as a white oil. Yield: 2.2 g (86%); 255 (M+H).

Workup

  1. customAt the end, reaction mixture
  2. concentrationwas concentrated
  3. washThe column was eluted with hexane (500 ml) and later with 25% ethyl acetate

Sources & evidence

ORD record
ord-a8a2a76479164780830086af12abf95c
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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