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

HRID 907644

反応式

HRID 907644 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 53628436CID 53628436触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-ac709544bcf24551afee16d3db6e9c86
出典データセット
uspto-grants-2011_09
特許番号
US08013183B2

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