Water → [2-Methyl-3-(thiophen-2-yl)phenyl]methanol

HRID 2295852ノート

反応式

HRID 2295852 の反応式
[CH3:1][C:2]1[C:10]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(OCC)C.O.[Cl-].[Na+]>O1CCCC1>[CH3:1][C:2]1[C:10]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

参加物

6

反応物 4

HCID 962Water2 回HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 132434172-Methyl-3-(thiophen-2-yl)benzoic acid

生成物 1

HCID 13243418[2-Methyl-3-(thiophen-2-yl)phenyl]methanol収率 99.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under an argon atmosphere, a stirred solution of 5.7 g (0.026 mol) of 2-methyl-3-(2-thienyl)benzoic acid in 50 mL of tetrahydrofuran was cooled to 0° C.±2° C. To this solution was added dropwise 4.4 g (0.051 mol, 51.3 mL of a 1.0 M solution) of borane tetrahydrofuran complex. The addition was made over 35 minutes. The reaction mixture was stirred for 0.5 hour at ambient temperature, then for two hours at reflux temperature. The reaction mixture was cooled, and 100 mL of diethyl ether saturated with water, then 20 mL of water, were cautiously added. The mixture was transferred to a separatory funnel containing 50 mL of ice, and was saturated with solid sodium chloride, and extracted with three portions of 200 mL each of diethyl ether. The combined extracts were dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give 5.3 g of 2-methyl-3-(2-thienyl)phenylmethanol as an oil.

後処理

  1. additionThe addition
  2. temperaturefor two hours at reflux temperature
  3. temperatureThe reaction mixture was cooled
  4. customThe mixture was transferred to a separatory funnel
  5. extractionextracted with three portions of 200 mL each of diethyl ether
  6. dry with materialThe combined extracts were dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure

出典と根拠

ORDレコード
ord-2de8797c9f22414bbbeedc2d225c56dc
出典データセット
uspto-grants-1984_01
特許番号
US04426524

反応ノート

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