Diazomethane → Methyl 2,6-dihydroxy-4-pentylbenzoate

HRID 488671노트

반응식

HRID 488671 반응식
[OH:1][C:2]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:8]=[C:7]([OH:16])[C:3]=1[C:4]([OH:6])=[O:5].[N+](=[CH2:19])=[N-]>CCOCC>[OH:1][C:2]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:8]=[C:7]([OH:16])[C:3]=1[C:4]([O:6][CH3:19])=[O:5]

참가 물질

4

반응물 2

HCID 9550DiazomethaneHCID 3046173Benzoic acid, 2,6-dihydroxy-4-pentyl-

생성물 1

HCID 22271912Methyl 2,6-dihydroxy-4-pentylbenzoate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 2,6-dihydroxy-4-pentylbenzoic acid (2.0 g, 8.9 mM) in ether was treated with a 0.3 M solution of diazomethane in ether (30 mL) and stirred for 10 minutes. Nitrogen was bubbled through the solution for 10 minutes and then glacial acetic acid (4 drops). The reaction was concentrated under reduced pressure and purified by chromatography (5% ethyl acetate in hexanes) to give the desired product. MS ESI(−)) m/e 237 (M−H)+; 1H NMR (300 MHz, CDCl3) δ 9.62 (bs, 2H), 6.33 (s, 2H), 4.06 (s, 3H), 2.50 (t, 2H), 1.64-1.55 (m, 2H), 1.34-1.27 (m, 4H), 0.92-0.87 (m, 3H).

후처리

  1. customNitrogen was bubbled through the solution for 10 minutes
  2. concentrationThe reaction was concentrated under reduced pressure
  3. custompurified by chromatography (5% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-5fb5e418febd41c7b9ce1a8113a7047f
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06972340B2

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