Benzyl Bromide → Benzyl pent-4-ynoate

HRID 1725997노트

반응식

HRID 1725997 반응식
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].C([O-])([O-])=O.[K+].[K+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.O>[C:1]([O:7][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5]

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 224644-Pentynoic acid

생성물 1

HCID 561097Benzyl pent-4-ynoate수율 100%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-pentynoic acid (5.25 g, 53.5 mmol) in DMF (107 mL) was treated with K2CO3 (11.09 g, 80.3 mmol) and benzyl bromide (6.37 mL, 53.5 mmol), stirred for 24 hours, diluted with water (200 mL), and extracted with diethyl ether (3×150 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography to provide the desired product (10.07 g, 100%). MS (ESI(+)) m/e 206 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 7.37 (m, 5H), 5.12 (s, 2H), 2.61 (t, 1H), 2.57 (m, 2H), 2.42 (m, 2H).

후처리

  1. extractionextracted with diethyl ether (3×150 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-b4693974fceb44688bed847758edd695
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491718B2

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