Water → cis-4-Tetrahydropyranyloxy 2-cyclopentenol

HRID 2552

反応式

HRID 2552 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[CH2:12][C@H:11]([O:13]C(=O)C)[CH:10]=[CH:9]1.O.[OH-].[Li+].COC(C)(C)C.O>C1COCC1.CO.O.C(Cl)(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[CH2:12][C@H:11]([OH:13])[CH:10]=[CH:9]1

参加物

7

反応物 4

HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 168937Lithium hydroxide, monohydrateHCID 13623284(+)-Acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester

生成物 1

HCID 13623252cis-4-Tetrahydropyranyloxy 2-cyclopentenol収率 93%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

Dissolve (-)-acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester (106 mg, 0.47 mmol, prepared in example 11) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (0.57 mmol) with stirring. After stirring for about 3 hours at room temperature, dilute the reaction with tert-butyl methyl ether (10 mL) and water (10 mL). Extract with tert-butyl methyl ether (2×10 mL). Combine the organic extracts, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 2.5 g, 1.7×2.5 cm column, 50% ethyl acetate/hexane, 150 mL) to provide the title compound (80 mg, 93% yield), [α]20D =+9.9°, (c=0.98, chloroform).

後処理

  1. additiondilute
  2. extractionExtract with tert-butyl methyl ether (2×10 mL)
  3. dry with materialCombine the organic extracts, dry over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customPurify the residue by flash chromatography (silica gel, 2.5 g, 1.7×2.5 cm column, 50% ethyl acetate/hexane, 150 mL)

出典と根拠

ORDレコード
ord-73c1b39d43c34bba9c7f0a1fb0614d7e
出典データセット
uspto-grants-1998_03
特許番号
US05728899

関連ノート

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