4-[3-(benzyloxy)-5-fluorophenyl]-4-formyl-3,4,5,6-tetrahydro-2H-pyran → 4-[3-(Benzyloxy)-5-fluorophenyl]-4-(1-hydroxyethyl)-3,4,5,6-tetrahydro-2H-pyran

HRID 1108070Notes

Reaction equation

HRID 1108070 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2([CH:22]=[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.[CH3:24][Mg]Br>C1COCC1.[Cl-].[NH4+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2([CH:22]([OH:23])[CH3:24])[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

5

Reactant 2

HCID 187863774-[3-(benzyloxy)-5-fluorophenyl]-4-formyl-3,4,5,6-tetrahydro-2H-pyranHCID 178418573HCID 178418573, compound

Product 1

HCID 187863634-[3-(Benzyloxy)-5-fluorophenyl]-4-(1-hydroxyethyl)-3,4,5,6-tetrahydro-2H-pyranYield 63.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred solution of 4-[3-(benzyloxy)-5-fluorophenyl]-4-formyl-3,4,5,6-tetrahydro-2H-pyran (1.08 g, 3.4 mmol) in THF (16 ml) at room temperature under a nitrogen atmosphere was added on 0.96 M solution of methyl magnesium bromide (5.3 ml, 5.1 mmol) in a dropwise manner. The mixture was stirred overnight, diluted with saturated aqueous ammonium chloride (40 ml) and extracted with dichloromethane (2×40 ml). The combined organic layers were washed with water (40 ml) and brine (40 ml), dried (magnesium sulfate) and concentrated to dryness. Purification by column chromatography (silica-gel, 150 g, ethyl acetate in n-hexane as an eluent increasing the amount of ethyl acetate from 40% to 60%) afforded the titled compound as a colorless liquid (0.71 g, 63%).

Workup

  1. extractionextracted with dichloromethane (2×40 ml)
  2. washThe combined organic layers were washed with water (40 ml) and brine (40 ml)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated to dryness
  5. customPurification by column chromatography (silica-gel, 150 g, ethyl acetate in n-hexane as an eluent
  6. temperatureincreasing the amount of ethyl acetate from 40% to 60%)

Sources & evidence

ORD record
ord-c31ff9522ea9444884139d6fa4203ce5
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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