Tetrahydrofuran → Methyl 3-hydroxy-5-{[(3S)-oxolan-3-yl]oxy}benzoate

HRID 548736Notes

Reaction equation

HRID 548736 reaction equation
C1(C[O:8][C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([O:19][C@H:20]3[CH2:24][CH2:23][O:22][CH2:21]3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])C=CC=CC=1.C1COCC1>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][C@H:20]2[CH2:24][CH2:23][O:22][CH2:21]2)[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 59127128Methyl 3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate

Product 1

HCID 59127189Methyl 3-hydroxy-5-{[(3S)-oxolan-3-yl]oxy}benzoateYield 96.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (1.2 g) was added to a mixture of methyl 3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate (12 g, 36.54 mmol), in ethanol (80 mL) and THF (80 mL) in an argon filled flask. The flask was evacuated and the atmosphere replaced with hydrogen. The mixture was stirred for 20 hours, filtered through Celite® and the solvent removed in vacuo to give the desired compound as a white solid (8.41 g).

Workup

  1. customThe flask was evacuated
  2. filtrationfiltered through Celite®
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b46b8fb721504033b724e63c556c5606
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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