Boron trifluoride etherate → (2s)-6-Benzyloxy-1-(4-fluorophenoxy)-hex-4-yn-2-ol

HRID 381627

반응식

HRID 381627 반응식
[CH2:1]([O:8][CH2:9][C:10]#[CH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.CCCCCC.B(F)(F)F.CC[O:29]CC.C1O[C@H]1CO.[F:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][C:45]2C=CC(F)=[CH:47][CH:46]=2)=[CH:40][CH:39]=1>C1COCC1>[CH2:1]([O:8][CH2:9][C:10]#[C:11][CH2:47][C@H:46]([OH:29])[CH2:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([F:37])=[CH:39][CH:40]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 8000Boron trifluoride etherateHCID 8058HexaneHCID 6917484((Prop-2-yn-1-yloxy)methyl)benzeneHCID 131722895(S)-glycidol 4-fluorophenyl etherHCID 178418339Butyllithium

생성물 1

HCID 59904762(2s)-6-Benzyloxy-1-(4-fluorophenoxy)-hex-4-yn-2-ol수율 65%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of benzyloxy prop-2-yne (2.3 g, 16 mmol) in dry THF (25 ml) at −78° C. was added n-BuLi in hexane (10.7 ml, 16 mmol) and the mixture stirred for 20 min. Borontrifluoride etherate (2 ml, 16 mmol) was then added to the solution and stirring continued for 20 min. at −78° C. A THF solution of (S)-glycidol-4-fluorophenyl ether (1.8 g, 10.7 mmol) was added and after stirring for 1 h at −78° C., the reaction was quenched by adding aqueous NH4Cl. The organic materials were extracted with ethyl acetate, dried (Na2SO4) and concentrated under vacuum. The crude product was purified on a silica gel column using EtOAc-light petroleum (1:4) as eluent to give (2S)-6-benzyloxy-1-(4-fluorophenoxy)-hex-4-yn-2-ol (2 g, 65%) as a yellow colour liquid. TLC:ethyl acetate-light petroleum (1:3), Rf=0.4. 1H NMR (CDCl3, 200 MHz): 82.65 (m, 2H), 3.95-4.10 (m, 2H), 4.13-4.21 (m, 3H), 4.6 (s, 2H), 6.8-7.02 (m, 4H), 7.30-7.38 (m, 5H).

후처리

  1. stirringstirring
  2. waitcontinued for 20 min. at −78° C
  3. stirringafter stirring for 1 h at −78° C.
  4. customthe reaction was quenched
  5. additionby adding aqueous NH4Cl
  6. extractionThe organic materials were extracted with ethyl acetate
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under vacuum
  9. customThe crude product was purified on a silica gel column

출처 및 근거

ORD 기록
ord-05cce9dd9dc1402b8ad62c16aa766e9e
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306895B1

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