Acetic Acid → HCID 10704760、化合物

HRID 1700956ノート

反応式

HRID 1700956 の反応式
C[Li].[Si:3]([O:10][C@H:11]1[CH2:16][CH2:15][O:14][C:12]1=[O:13])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[C:17](O)(=O)C.C(=O)(O)[O-].[Na+]>C(OCC)C.C1COCC1>[Si:3]([O:10][C@H:11]1[CH2:16][CH2:15][O:14][C:12]1([OH:13])[CH3:17])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 10965951(S)-2-(tert-Butyldimethylsilyloxy)-g-butyrolactoneHCID 178418348HCID 178418348、化合物

生成物 1

HCID 10704760HCID 10704760、化合物収率 100.1%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Methyl lithium (670 μl [1.11 mmol, 1.1 equiv] of a 1.65 M solution in diethyl ether) is added dropwise to a stirred solution of (S)-2-(tertbutyidimethylsilyloxy)-γ-butyrolactone 12 (218 mg, 1.01 mmol) in THF (4.0 ml) cooled to −78° C. is added dropwise. After stirring at −78° C. for 3 h, the reaction is quenched by the addition of glacial acetic acid (72 μl, 1.26 mmol, 1.25 equiv). Diethyl ether (20 ml) and saturated aqueous sodium bicarbonate solution (10 ml) are added. After stirring for 5 min the organic layer is separated and the aqueous layer is extracted with diethyl ether (2×20 ml). The combined organic extracts are dried over magnesium sulfate and concentrated in vacua. Crude (3S)-3-(tertbutyidimethylsilyloxy)-2-hydroxy-2-methyl-tetrahydrofurane 13 (235 mg, 93%) is obtained as a colourless crystalline solid (mixture of diastereomers) which is used for the synthesis of (S)-3,5-di-(tert-butyldimethylsilyloxy)-pentan-2-one 14 without further purification.

後処理

  1. additionis added dropwise
  2. stirringAfter stirring for 5 min the organic layer
  3. customis separated
  4. extractionthe aqueous layer is extracted with diethyl ether (2×20 ml)
  5. dry with materialThe combined organic extracts are dried over magnesium sulfate
  6. concentrationconcentrated in vacua

出典と根拠

ORDレコード
ord-5ea315a495474b1492ddbfbd23634523
出典データセット
uspto-grants-2002_02
特許番号
US06350878B1

反応ノート

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