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Hydrochloric Acid → HCID 9800248, 화합물

HRID 1764970
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HRID 1764970 반응식
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[CH2:14][CH2:15][C:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C:18](=[O:28])[CH:17]=4)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].Cl>O1CCCC1>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[CH2:14][CH2:15][C:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C@H:18]([OH:28])[CH:17]=4)[CH2:11][CH2:10]1)[CH3:8])[CH3:1].[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[CH2:14][CH2:15][C:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C@@H:18]([OH:28])[CH:17]=4)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3611392Lithium tri-s-butylborohydrideHCID 15871124HCID 15871124, 화합물

생성물 2

HCID 9800248HCID 9800248, 화합물HCID 9800249HCID 9800249, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

실험 절차

To a solution of 520 mg cholesta-4,8-dien-3-one in 45 ml tetrahydrofuran 1.70 ml of a L-Selectride solution (1 N, in tetrahydrofuran) are added dropwise at −75° C. The reaction mixture is warmed to room temperature within 4 hours, poured into hydrochloric acid (1 N) and extracted with ethyl acetate. The organic layer is separated, washed with brine, dried over anhydrous sodium sulphate and filtered. After evaporation of the solvent the residue is chromatographed with a mixture of hexane and ethyl acetate to give 286 mg cholesta-4,8-dien-3β-ol and 20 mg cholesta-4,8-dien-3α-ol as white solids.

후처리

  1. extractionextracted with ethyl acetate
  2. customThe organic layer is separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customAfter evaporation of the solvent the residue
  7. customis chromatographed with a mixture of hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-cd4a606e533444f5aaa6ed0b9c6a8e4d
출처 데이터셋
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
USRE039678E1

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