Ethyl Acetate → HCID 21107247, compound

HRID 1870003Notes

Reaction equation

HRID 1870003 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH:13]=[CH2:14])[CH:12]=1)[C:9](=[O:15])[CH2:8][CH2:7][C:6]2([CH3:17])[CH3:16].[N+](=[CH2:20])=[N-].C(OCC)(=O)C>C(OCC)C.CCCCCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:13]1([C:11]2[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]3[C:10]=2[C:9](=[O:15])[CH2:8][CH2:7][C:6]3([CH3:17])[CH3:16])[CH2:20][CH2:14]1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 9550DiazomethaneHCID 21107234HCID 21107234, compound2×

Product 1

HCID 21107247HCID 21107247, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-25 °C

Procedure

A stirred, cooled (−40° C.) solution of 6-methoxy-4,4-dimethyl-8-vinyl-3,4-dihydro-2H-naphthalen-1-one (Intermediate 155, 51.7 g, 7.4 mmol) in diethyl ether (10 mL) was treated with a solution of diazomethane in ether (40 mmol in 50 mL of ether) followed by palladium(II) acetate (0.08 g) and the resulting reaction mixture was warmed to −25° C. when effervescence was observed. The reaction mixture was then filtered through a plug of silica and the filtrate was evaporated to afford a dark brown residue that was subjected to flash column chromatography over silica gel (23-400 mesh) using 20% ethyl acetate in hexane as the eluent to afford the title product as a pale yellow solid (1.5 g, 83%).

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was then filtered through a plug of silica
  3. customthe filtrate was evaporated
  4. customto afford a dark brown residue that

Sources & evidence

ORD record
ord-eaab8c1d30fe4098837b63e36a5df2f2
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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