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Hydrochloric Acid → (3aR,4S,5R,6aS)-4-(tert-Butyldimethylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one

HRID 371446
ノート
印刷プレビュー

反応式

HRID 371446 の反応式
C(=O)([O-])[O-].[K+].[K+].[Si:7]([O:14][CH2:15][C@H:16]1[C@H:23]([O:24]C(=O)C2C=CC=CC=2)[CH2:22][C@H:21]2[C@@H:17]1[CH2:18][C:19](=[O:33])[O:20]2)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].Cl>CO>[Si:7]([O:14][CH2:15][C@H:16]1[C@H:23]([OH:24])[CH2:22][C@H:21]2[C@@H:17]1[CH2:18][C:19](=[O:33])[O:20]2)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2724503(3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

生成物 1

HCID 10613232(3aR,4S,5R,6aS)-4-(tert-Butyldimethylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one収率 76.4%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

1.845 g of anhydrous potassium carbonate is introduced into a solution of 11.716 g of the silyl ether produced in Example 1 in 122 ml of absolute MeOH, and the mixture is agitated under argon for 3 hours. The reaction solution is then cooled in an ice bath and gently combined dropwise with 1.86 ml of concentrated hydrochloric acid. Excess methanol is extensively concentrated under vacuum at room temperature, the residue is combined with 300 ml of methylene chloride, and the solution is dried over magnesium sulfate, filtered off, and concentrated. The oily residue is made to crystallize by trituration with hexane, thus obtaining 6.562 g of the title compound, mp 60.7° C.

後処理

  1. temperatureThe reaction solution is then cooled in an ice bath
  2. concentrationExcess methanol is extensively concentrated under vacuum at room temperature
  3. dry with materialthe solution is dried over magnesium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated
  6. customto crystallize by trituration with hexane

出典と根拠

ORDレコード
ord-7f63074b83494eb291fe191d514c5e0a
出典データセット
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04532236

反応ノート

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