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]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
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 TEF 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): 8 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
- stirringstirring
- waitfor 20 min. at −78° C
- stirringafter stirring for 1 h at −78° C.
- customthe reaction was quenched
- additionby adding aqueous NH4Cl
- extractionThe organic materials were extracted with ethyl acetate
- dry with materialdried (Na2SO4)
- concentrationconcentrated under vacuum
- customThe crude product was purified on a silica gel column
Sources & evidence
- ORD record
- ord-56b42bfcb0974c2ab2e15fa56c90da68
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06566538B1
Linked notes
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