HCID 22650065, compound → HCID 11768601, compound

HRID 2305283Notes

Reaction equation

HRID 2305283 reaction equation
[H][H].[O:3]1[CH:9]2[CH:4]1[C:5]([O:7][C:8]2([CH3:11])[CH3:10])=[O:6]>[Pd].O1CCCC1>[OH:3][CH:9]1[C:8]([CH3:11])([CH3:10])[O:7][C:5](=[O:6])[CH2:4]1

Participants

5

Reactant 2

HCID 22650065HCID 22650065, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11768601HCID 11768601, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In dioxane, 2-hydroxy-4,4-dimethyl-γ-butyrolactone prepared in the same manner as in Production Example 10 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 30%. The prepared α,β-unsaturated-γ-butyrolactone was then allowed to react with m-chloroperbenzoic acid (MCPBA) in methylene chloride at room temperature to yield 2,3-epoxy-4,4-dimethyl-γ-butyrolactone in a yield of 85%. Hydrogen was bubbled in a mixture of 10 mmole of the above-prepared 2,3-epoxy-4,4-dimethyl-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-4,4-dimethyl-γ-butyrolactone in a yield of 63%.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-5cf8b4f485344feda0bd2535ae83cc37
Source dataset
uspto-grants-2002_08
Patent number
US06440636B1

Reaction notes

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