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

HRID 656694ノート

反応式

HRID 656694 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
4 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5b99079d99e04a24af48a5ee0836f1c8
出典データセット
uspto-grants-2011_12
特許番号
US08071796B2

反応ノート

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