Hydrochloric Acid → (+/-)-3-(2,4-Dihydroxyphenyl)-1-methylcyclohexanol

HRID 2307161ノート

反応式

HRID 2307161 の反応式
[CH3:1][Mg]Cl.[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:12]1[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[CH2:13]1.Cl>O1CCCC1>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:12]1[CH2:17][CH2:16][CH2:15][C:14]([CH3:1])([OH:18])[CH2:13]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 12788196(+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanoneHCID 178418332HCID 178418332、化合物

生成物 1

HCID 22337786(+/-)-3-(2,4-Dihydroxyphenyl)-1-methylcyclohexanol収率 28%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Methyl magnesium chloride (0.132 ml of a 22% w/w solution in tetrahydrofuran) was added to a solution of (±)-3-(2,4-dihydroxyphenyl)cyclohexanone (20 mg) in tetrahydrofuran (3 ml) at 0° C. under argon. After 16 hr, dilute hydrochloric acid (1 ml) was added dropwise and the reaction mixture was partitioned between ethyl acetate (50 ml) and brine (50 ml). The aqueous layer was extracted with ethyl acetate (2×50 ml), and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The crude residue was purified by preparative HPLC to furnish the title compound as a white solid (6 mg, 28%). δH (d4-MeOH) 1.20 (3H, s), 1.22-1.39 (2H, overlapping m), 1.46 (1H, t), 1.54-1.87 (5H, overlapping m), 3.22 (1H, m), 6.19-6.25 (2H, overlapping m), 6.86 91H, d); m/z (ES−) 281 (M+60−H)−.

後処理

  1. customthe reaction mixture was partitioned between ethyl acetate (50 ml) and brine (50 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe crude residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-74f247b612f24067917fe9e38c937fc0
出典データセット
uspto-grants-2004_12
特許番号
US06828460B2

反応ノート

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