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

HRID 2304118Notes

Reaction equation

HRID 2304118 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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): δ 2.65 (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).

Workup

  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

Sources & evidence

ORD record
ord-61ad642ed5da4c268ba87820fb862823
Source dataset
uspto-grants-2002_08
Patent number
US06433197B1

Reaction notes

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