Methanol → Methyl (oxan-4-yl)acetate

HRID 2053591Notes

Reaction equation

HRID 2053591 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[CH3:6][OH:7]>[Pd]>[CH3:6][O:7][C:3](=[O:4])[CH2:2][CH:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:1]1

Participants

4

Reactant 2

HCID 887MethanolHCID 8028Tetrahydrofuran

Product 1

HCID 46738768Methyl (oxan-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 303 (490 mg, 3.1 mmol) in 1:1 THF:MeOH (10 mL) is added 10% palladium-on-carbon (74 mg), and the mixture is stirred at RT under hydrogen for 16 h. The mixture is filtered, and the filtrate is evaporated to give 481 mg of the product 304. 1H NMR (CDCl3) δ 4.0-3.9 (m, 2H), 3.70 (s, 3H), 3.40 (t, 2H), 2.25 (d, 2H), 2.01 (m, 1H), 1.65-1.60 (m, 2H), 1.40-1.25 (m, 2H); MS: m/z 159 (M++1).

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-e023879730bf4d21b7cd3911d5c4acb5
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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