Perfluoro-1-butanesulfonyl fluoride → HCID 57927655, compound

HRID 889145Notes

Reaction equation

HRID 889145 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10](O)[CH2:11][O:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[F:44]C(F)(C(F)(F)F)C(F)(F)C(F)(F)S(F)(=O)=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][C@H:10]([F:44])[CH2:11][O:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11729567HCID 11729567, compound

Product 1

HCID 57927655HCID 57927655, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After dissolving (R)-1-benzyloxy-3-trityloxypropan-2-ol (CAS 83526-68-5) (10.45 g) in toluene (50 ml), nonafluoro-1-butanesulfonyl fluoride (7.95 ml) was added and the mixture was cooled on ice. Next, 1,8-diazabicyclo[5.4.0]undeca-7-ene (6.63 ml) was added dropwise while stirring. The mixture was stirred for 30 minutes on ice, and then for 3 hours and 30 minutes at room temperature. The reaction mixture was directly purified by silica gel column chromatography to obtain the title compound (7.52 g).

Workup

  1. additionwas added
  2. temperaturethe mixture was cooled on ice
  3. stirringThe mixture was stirred for 30 minutes on ice
  4. custom30 minutes
  5. customat room temperature
  6. customThe reaction mixture was directly purified by silica gel column chromatography

Sources & evidence

ORD record
ord-48bf30a3c8614c3db69385e99933b98b
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

Loading…