HCID 22650068, compound → HCID 22650074, compound

HRID 2305284Notes

Reaction equation

HRID 2305284 reaction equation
[H][H].[O:3]1[C:9]2([CH3:10])[CH:4]1[C:5]([O:7][C:8]2([CH3:12])[CH3:11])=[O:6]>[Pd].O1CCCC1>[OH:3][C:9]1([CH3:10])[C:8]([CH3:12])([CH3:11])[O:7][C:5](=[O:6])[CH2:4]1

Participants

5

Reactant 2

HCID 22650068HCID 22650068, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22650074HCID 22650074, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

By using ethyl crotonate instead of ethyl acrylate, 2 hydroxy-3,4,4-trimethyl-γ-butyrolactone was prepared in a yield of 15% in the same manner as in Production Example 10. The prepared 2-hydroxy-3,4,4-trimethyl-γ-butyrolactone was subjected to a reaction (dehydration reaction) with equivalent P2O5 at room temperature to yield a corresponding α,β-unsaturated-γ-butyrolactone in a yield of 34%. This compound was then allowed to react with m-chloroperbenzoic acid (MCPBA) in methylene chloride at room temperature to yield 2,3epoxy-3,4,4-trimethyl-γ-butyrolactone in a yield of 75%. Hydrogen was bubbled in a mixture of 10 mmole of the above-prepared 2,3-epoxy-3,4,4-trimethyl-γ-butyrolactone, 1 g of a 5% by weight Pd-C, and 20 ml of tetrahydrofuran at room temperature for 11 hours. The reaction mixture was filtrated and was concentrated, and the concentrate was subjected to column chromatography on a silica gel to yield 3-hydroxy-3,4,4-trimethyl-γ-butyrolactone in a yield of 82%.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-2c1bfaa33b464766ba854118f87dbd82
Source dataset
uspto-grants-2002_08
Patent number
US06440636B1

Reaction notes

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