Benzoic Acid → Cyano-(6-methoxy-3,3-dimethyl-5-prop-2-ynyloxy-indan-1-ylidene)-acetic acid ethyl ester

HRID 2228352Notes

Reaction equation

HRID 2228352 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:14])([CH3:13])[CH2:8][C:9]2=O)=[CH:5][C:4]=1[O:15][CH2:16][C:17]#[CH:18].[CH3:19][CH2:20][O:21][C:22]([CH2:24][C:25]#[N:26])=[O:23].N1CCCC1.C(O)(=O)C1C=CC=CC=1>C1(C)C(C)=CC=CC=1.O>[CH2:20]([O:21][C:22](=[O:23])[C:24]([C:25]#[N:26])=[C:9]1[C:10]2[C:6](=[CH:5][C:4]([O:15][CH2:16][C:17]#[CH:18])=[C:3]([O:2][CH3:1])[CH:11]=2)[C:7]([CH3:14])([CH3:13])[CH2:8]1)[CH3:19]

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 7764Ethyl cyanoacetateHCID 31268PyrrolidineHCID 184695826-Methoxy-3,3-dimethyl-5-prop-2-ynyloxy-indan-1-one

Product 1

HCID 53867743Cyano-(6-methoxy-3,3-dimethyl-5-prop-2-ynyloxy-indan-1-ylidene)-acetic acid ethyl esterYield 20.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

The above 6-methoxy-3,3-dimethyl-5-prop-2-ynyloxy-indan-1-one (2.44 g) was treated with 1.13 g of ethyl cyano acetate in the presence of 0.1 equivalents of pyrrolidine and benzoic acid in 20 ml of xylene. The reaction mixture was refluxed for 30 hours with simultaneous separation of water. Then, the cold reaction mixture was washed with water, concentrated and chromatographed in hexane/ethyl acetate through SiO2 to yield 0.7 g of yellow crystals. m.p. 132-136° C. UV 362 nm (ε=23′222), MS: 339(M+), 324, 300 (100%).

Workup

  1. customThen, the cold reaction mixture
  2. washwas washed with water
  3. concentrationconcentrated
  4. customchromatographed in hexane/ethyl acetate through SiO2

Sources & evidence

ORD record
ord-b4834fbdde0e482d9b81e85d89997b96
Source dataset
uspto-grants-2002_07
Patent number
US06416746B1

Reaction notes

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