Potassium Carbonate → [4-Chloro-2-(cyclopropylmethoxy)phenyl]methanol

HRID 514456

反応式

HRID 514456 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([OH:8])[CH:7]=1.Br[CH:12]([CH:14]1[CH2:16][CH2:15]1)O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([O:8][CH2:12][CH:14]2[CH2:16][CH2:15]2)[CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 3271485-Chloro-2-(hydroxymethyl)phenolHCID 53647370HCID 53647370、化合物

生成物 1

HCID 86725580[4-Chloro-2-(cyclopropylmethoxy)phenyl]methanol収率 13.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Charged 5-chloro-2-(hydroxymethyl)phenol (616 mg, 3.88 mmol, PREPARATION 7), bromocyclopropylmethanol (525 mg, 3.88 mmol), K2CO3 (1.07 g, 7.77 mmol) and DMF (6 mL) to a flask, purged with nitrogen and heated to 80° C. overnight. Poured into ice water, and extracted with ethyl acetate twice, and washed the organic phase with water twice, brine and dried with anhydrous Na2SO4, removed the solvent for silica gel chromatograph to give 108 mg of the title compound (13%). 1H NMR (400 MHz, CDCl3): δ 0.33-0.37 (2H, m), 0.63-0.68 (2H, m), 1.26-1.28 (1H, m), 3.84 (2H, d, J=7.2 Hz), 4.67 (2H, s), 4.86 (1H, s), 6.84 (1H, d, J=1.2 Hz), 6.91 (1H, dd, J=2.0 Hz, 8.0 Hz), 7.19 (1H, d, J=7.6 Hz).

後処理

  1. custompurged with nitrogen
  2. additionPoured into ice water
  3. extractionextracted with ethyl acetate twice
  4. washwashed the organic phase with water twice
  5. dry with materialbrine and dried with anhydrous Na2SO4
  6. customremoved the solvent for silica gel chromatograph

出典と根拠

ORDレコード
ord-3e0df4d096ce4d8c87798068740605b8
出典データセット
uspto-grants-2015_08
特許番号
US09107916B2

関連ノート

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