Acetic Acid → HCID 10704760, 화합물

HRID 1700956

반응식

HRID 1700956 반응식
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]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 10965951(S)-2-(tert-Butyldimethylsilyloxy)-g-butyrolactoneHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 10704760HCID 10704760, 화합물수율 100.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ea315a495474b1492ddbfbd23634523
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350878B1

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