Dimethylformamide → 5-Hydroxy-6-methoxy-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

HRID 2228350Notes

Reaction equation

HRID 2228350 reaction equation
C(OC(=O)C(C#N)=[C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:17]C)=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([CH3:20])([CH3:19])[CH2:7]1)C.[C-]#N.[Na+].CN(C)C=[O:30]>>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9]([C:8]([CH3:20])([CH3:19])[CH2:7][C:6]2=[O:30])=[CH:10][C:11]=1[OH:17]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 54568492Cyano-(2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-ylidene)acetic Acid Ethyl Ester

Product 1

HCID 134808615-Hydroxy-6-methoxy-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

Conditions

Temperature
100 °C

Procedure

In a three necked reaction flask equipped with a reflux condenser, a mixture of 5 g of 2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-one (see example 1) and 5.5 g of sodium cyanide in 44.5 ml of dimethyl formamide was stirred at 100° C. for 40 hours. Then, the mixture was pored on an aqueous NaH2PO4 solution and extracted 4 times with ethyl acetate, dried over Na2CO3, and concentrated. The raw product was chromatographed in methylene chloride containing 1% of methanol to yield 2.5 g of white crystals. m.p. 105-107° C. MS: 206(M+), 191(100%), 163, 131, 103.

Workup

  1. customIn a three necked reaction flask equipped with a reflux condenser
  2. extractionextracted 4 times with ethyl acetate
  3. dry with materialdried over Na2CO3
  4. concentrationconcentrated
  5. customThe raw product was chromatographed in methylene chloride containing 1% of methanol

Sources & evidence

ORD record
ord-2f17f58e3d3a4fb2a08351fd1307557f
Source dataset
uspto-grants-2002_07
Patent number
US06416746B1

Reaction notes

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