ethyl 4-(3-benzyloxy-5-fluorophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate → 4-[3-(Benzyloxy)-5-fluorophenyl]-4-hydroxymethyl-3,4,5,6-tetrahydro-2H-pyran

HRID 1108068Notes

Reaction equation

HRID 1108068 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2([C:22](OCC)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2([CH2:22][OH:23])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 18786326ethyl 4-(3-benzyloxy-5-fluorophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 187863144-[3-(Benzyloxy)-5-fluorophenyl]-4-hydroxymethyl-3,4,5,6-tetrahydro-2H-pyranYield 94.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of ethyl 4-[3-(benzyloxy)-5-fluorophenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (1.54 g, 4.3 mmol) in ether (150 ml) was added lithium aluminium hydride (0.16 g, 4.3 mmol) in three portions. The resulting suspension was stirred at room temperature under a nitrogen atmosphere for 20 min. Excess of hydride was destroyed by adding saturated aqueous sodium sulfate. The mixture was diluted with 10% aqueous sulfuric acid (100 ml) and the organic layer was separated. The ethereal layer was washed with water (100 ml), saturated aqueous sodium bicarbonate (100 ml) and brine (100 ml), dried (magnesium sulfate) and concentrated to dryness to afford the titled compound as white solids (1.28 g, 94%).

Workup

  1. customExcess of hydride was destroyed
  2. additionby adding saturated aqueous sodium sulfate
  3. additionThe mixture was diluted with 10% aqueous sulfuric acid (100 ml)
  4. customthe organic layer was separated
  5. washThe ethereal layer was washed with water (100 ml), saturated aqueous sodium bicarbonate (100 ml) and brine (100 ml)
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-90eb606c93b34db79469f9283f8f2a09
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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