Tetrahydrofuran → HCID 68473560, 화합물

HRID 473072

반응식

HRID 473072 반응식
[CH3:1][C:2]1([CH2:16][O:17][Si:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20])[CH2:10][C:9]2[C:4](=[C:5]([CH3:14])[C:6]([CH:12]=[CH2:13])=[C:7]([CH3:11])[CH:8]=2)[CH:3]1[OH:15].B(C1CCCCC1)C1CCCCC1.C1C[O:41]CC1>>[OH:41][CH2:13][CH2:12][C:6]1[C:5]([CH3:14])=[C:4]2[C:9]([CH2:10][C:2]([CH3:1])([CH2:16][O:17][Si:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:3]2[OH:15])=[CH:8][C:7]=1[CH3:11]

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 15879360CID 15879360HCID 68475157HCID 68475157, 화합물

생성물 1

HCID 68473560HCID 68473560, 화합물수율 81%

실험 절차

To the stirred solution of compound 8 (0.85 g, 2.45 mmol) in dry THF was added (Cy)2BH (0.87 g, 4.91 mmol) slowly at 0° C. under argon atmosphere. The reaction mixture was warmed to room temperature and stirred for 12 h. The reaction mixture was quenched with 2N NaOH (6 mL) and H2O2 (3 mL) at 0° C. and allowed to stir for 4 h. Then crude reaction mixture was extracted with ethyl acetate (40 mL), washed with water (10 mL), brine (10 mL) dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 8 to 10% EtOAc in petroleum ether eluant) gave pure compound 9 (0.72 g, 81%) as gummy syrup.

후처리

  1. customThe reaction mixture was quenched with 2N NaOH (6 mL) and H2O2 (3 mL) at 0° C.
  2. stirringto stir for 4 h
  3. customThen crude reaction mixture
  4. extractionwas extracted with ethyl acetate (40 mL)
  5. washwashed with water (10 mL), brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customPurification by column chromatography (SiO2, 8 to 10% EtOAc in petroleum ether eluant)

출처 및 근거

ORD 기록
ord-ffcdd68e47104200a9b3c4395ec2e520
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633252B2

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