Ethyl acetate hexane → 3,3-Dimethyl-1,3-dihydroisobenzofuran-5-carbaldehyde

HRID 420338Notes

Reaction equation

HRID 420338 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2([CH3:12])[CH3:11])=[CH:4][CH:3]=1.CCCCCC.C[CH2:20][O:21]C(C)=O>>[CH3:11][C:8]1([CH3:12])[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([CH:20]=[O:21])[CH:10]=2)[CH2:6][O:7]1

Participants

3

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 578038426-Bromo-1,1-dimethyl-1,3-dihydro-2-benzofuran

Product 1

HCID 866395423,3-Dimethyl-1,3-dihydroisobenzofuran-5-carbaldehyde

Procedure

The title compound is prepared in analogous manner as described for example 47a from 6-bromo-1,1-dimethyl-1,3-dihydro-isobenzofuran to yield a light yellow oil: TLC (hexane-EtOAc 1:1) Rf=0.50; HPLC RtA=1.43 min; 1H NMR (400 MHz, CDCl3): δ10.02 (s, 1H), 7.78 (d, 1H), 7.65 (s, 1H), 7.36 (d, 1H), 5.11 (s, 2H), 1.53 (s, 9H).

Workup

  1. customto yield a light yellow oil
  2. customHPLC RtA=1.43 min

Sources & evidence

ORD record
ord-5822a97087434ad0a4e62ec0fb1c5f03
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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