Hydrochloric Acid → (1R)-2,2,2-trifluoro-1-(4-fluorophenyl)ethan-1-ol

HRID 907644

반응식

HRID 907644 반응식
C1(C)C=CC=CC=1.[F:8][C:9]([F:20])([F:19])[C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=[O:11].[B]1OC2C(=CC=CC=2)O1.Cl>O1CCBN1.C(OCC)(=O)C.ClCCl>[F:20][C:9]([F:8])([F:19])[C@@H:10]([C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[OH:11]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 6327445Benzcatechinborane

생성물 1

HCID 12640348(1R)-2,2,2-trifluoro-1-(4-fluorophenyl)ethan-1-ol수율 87.1%

시약·촉매·용매 3

HCID 53628436CID 53628436촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a −78° C. toluene (25 mL)/dichloromethane (25 mL) solution of 2,2,2,4′-tetrafluoroacetophenone (2.5 g, 13.01 mmol) and 1M S-methyl CBS oxazaborolidine catalyst (1.3 mL, 1.3 mmol) was added freshly distilled catecholborane (1.66 mL, 15.62 mmol). The reaction mixture was maintained at −78° C. for 16 h at which time 4N HCl (5 mL in dioxane) was added and the reaction mixture was allowed to warm to room temperature. The reaction mixture was diluted with ethyl acetate and washed with a saturated brine solution. The organic layer was dried over magnesium sulfate, filtered and concentrated to provide a solid. The solid was suspended in hexanes and filtered off. The hexanes filtrate containing the desired product was concentrated and the residue subjected to flash chromatography (10 hexanes:1 ethylacetate) to provide the title compound as colorless oil (2.2g, 87% yield). The ratio of enantiomers was determined to be 95:5 by chiral HPLC (Chiralcel OD column, 95 hexanes:5 isopropanol mobile phase. Ret. time major product 6.757 min. Ret. time minor isomer 8.274 min.).

후처리

  1. additionwas added
  2. washwashed with a saturated brine solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide a solid
  7. filtrationfiltered off
  8. additionThe hexanes filtrate containing the desired product
  9. concentrationwas concentrated

출처 및 근거

ORD 기록
ord-ac709544bcf24551afee16d3db6e9c86
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013183B2

연결된 노트

불러오는 중…