Water → HCID 89963253, 화합물

HRID 337880노트

반응식

HRID 337880 반응식
[H-].[Na+].[C@H:3]12[O:9][C@H:8]1[CH2:7][CH2:6][CH2:5][C@H:4]2[OH:10].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH2:19]>C1COCC1>[CH2:11]([O:10][C@:4]1([OH:19])[CH2:5][CH2:6][CH2:7][C@H:8]2[C@H:3]1[O:9]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 330105AC1L766H

생성물 1

HCID 89963253HCID 89963253, 화합물수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of sodium hydride (63%; 1.20 g, 31.5 mmol) in THF (20 mL), a solution of the (1R*,2R*,6S*)-7-oxabicyclo[4.1.0]heptan-2-ol (3.10 g, 27.2 mmol) prepared in Example 100a in THF (20 mL) was added with cooling on ice, and the mixture was stirred at room temperature for 1 hour. To the reaction solution, benzyl bromide (4.0 mL, 33.4 mmol) was added, and the mixture was stirred at room temperature for 12 hours. To the reaction solution, water (50 mL) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=4:1) to yield the title compound (2.85 g, 51%) as a light brown oil.

후처리

  1. temperaturewith cooling on ice
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. extractionfollowed by extraction with ethyl acetate (50 mL)
  4. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  5. concentrationAfter vacuum concentration
  6. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-16e1b8293e0647809ce88222feb558d7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889741B2

반응 노트

불러오는 중…