Water → (1S,4R)-4-(Benzyloxy)cyclopent-2-en-1-ol

HRID 2556

Reaction equation

HRID 2556 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([O:14]C(=O)C)[CH:11]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].O.C(Cl)(Cl)Cl>C1COCC1.CO.O>[CH2:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([OH:14])[CH:11]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 168937Lithium hydroxide, monohydrateHCID 86752290(-)-Acetic acid cis-4-benzyloxy-cyclopent-2-enyl ester

Product 1

HCID 15812323(1S,4R)-4-(Benzyloxy)cyclopent-2-en-1-olYield 92.8%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Dissolve (-)-acetic acid cis-4-benzyloxy-cyclopent-2-enyl ester (158 mg, 0.68 mmol, prepared in example 17) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (0.75 mmol) with stirring. After stirring for about 2 hours at room temperature, dilute the reaction with water (10 mL) and extract with tert-butyl methyl ether. Combine the organic phases, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 2 g, 20% ethyl acetate/hexane, 1.5×2.5 cm column) to provide the title compound (120 mg, 92% yield), [α]20D =+5.0°, (C=0.93, chloroform).

Workup

  1. additiondilute
  2. extractionextract with tert-butyl methyl ether
  3. dry with materialdry over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customPurify the residue by flash chromatography (silica gel, 2 g, 20% ethyl acetate/hexane, 1.5×2.5 cm column)

Sources & evidence

ORD record
ord-91b9cd4f6514451c9af570b41fa98ef5
Source dataset
uspto-grants-1998_03
Patent number
US05728899

Linked notes

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