Methanol → Methyl (oxan-4-yl)acetate

HRID 18798Notes

Reaction equation

HRID 18798 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, 2 H), 3.70 (s, 3 H), 3.40 (t, 2 H), 2.25 (d, 2 H), 2.01 (m, 1 H), 1.65-1.60 (m, 2 H), 1.40-1.25 (m, 2 H); MS: m/z 159 (M++1).

Workup

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

Sources & evidence

ORD record
ord-c6739d33926c4aaabfc5f5d42a964638
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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