Sodium Bicarbonate → 4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol

HRID 656694노트

반응식

HRID 656694 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:23])([CH3:22])[CH2:12][C:13]([OH:21])([C:17]([F:20])([F:19])[F:18])[C:14](O)=[O:15])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[Li].C([O-])(O)=O.[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:23])([CH3:22])[CH2:12][C:13]([C:17]([F:20])([F:18])[F:19])([OH:21])[CH2:14][OH:15])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 3028194LithiumHCID 667261154-(5-fluoro-2,3-dihydro-benzofuran-7-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic Acid

생성물 1

HCID 469395614-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol수율 73.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
4 °C

실험 절차

A solution of 6.6 mol 4-(5-fluoro-2,3-dihydro-benzofuran-7-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid in 77 ml of THF is cooled to 4° C. 12 mmol of lithium aluminumhydride is added portionwise to the solution. The mixture is stirred at 4° C. for 60 minutes, and stirred for 8-9 hours under reflux conditions. After complete reaction (TLC control) the mixture is cooled to 4° C. and treated with 1 ml of saturated NaHCO3 solution. The mixture is stirred for at least 2 hours whereupon the colour of the mixture turns from grey to white. The precipitated aluminium salts are filtered off and washed with 10 ml of hot THF. The solvent is evaporated under vacuum. The residue is purified by recrystallization from dichloromethane and n-heptane. (yield 73.7%).

후처리

  1. stirringstirred for 8-9 hours under reflux conditions
  2. customAfter complete reaction (TLC control) the mixture
  3. temperatureis cooled to 4° C.
  4. stirringThe mixture is stirred for at least 2 hours whereupon the colour of the mixture
  5. filtrationThe precipitated aluminium salts are filtered off
  6. washwashed with 10 ml of hot THF
  7. customThe solvent is evaporated under vacuum
  8. customThe residue is purified by recrystallization from dichloromethane and n-heptane

출처 및 근거

ORD 기록
ord-5b99079d99e04a24af48a5ee0836f1c8
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071796B2

반응 노트

불러오는 중…