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

HRID 1011786Notes

Reaction equation

HRID 1011786 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.C(O)C.[Pd]>[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 1

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

Product 1

HCID 59127189Methyl 3-hydroxy-5-{[(3S)-oxolan-3-yl]oxy}benzoateYield 75.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate (25.0 g, 76.2 mmol) was dissolved in THF (150 mL) and ethanol (150 mL). 10% Palladium on carbon (30 mg) was added and the mixture placed under a hydrogen atmosphere and left to stir at RT until the reaction was complete. The catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated in vacuo to give an orange oil which crystallised on standing. The solid was filtered off and washed with diethyl ether to give the desired product as a white solid (13.75 g).

Workup

  1. waitleft
  2. customThe catalyst was removed by filtration through diatomaceous earth
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give an orange oil which
  5. customcrystallised
  6. filtrationThe solid was filtered off
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-af666db8975544d4be6e7f19cf1166d4
Source dataset
uspto-grants-2011_07
Patent number
US07977328B2

Reaction notes

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