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

HRID 514456

반응식

HRID 514456 반응식
[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

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 3271485-Chloro-2-(hydroxymethyl)phenolHCID 53647370HCID 53647370, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3e0df4d096ce4d8c87798068740605b8
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107916B2

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