Salicylaldehyde → 2-(10-Undecynyloxy)benzaldehyde

HRID 620553

반응식

HRID 620553 반응식
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[CH:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:21]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]#[CH:11]

참가 물질

5

반응물 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 1171111-Undecyne, 11-bromo-

생성물 1

HCID 156174982-(10-Undecynyloxy)benzaldehyde

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To an ice-cold solution of 11-hydroxyundecyne (10 g, 59.4 mmoles) in 400 ml of methylene chloride under argon was added in one portion carbon tetrabromide (40.5 g, 0.1224 mole). The reaction mixture was stirred at 0° C. for 5 minutes and triphenylphosphine (29.43 g, 0.1122 mole) was added. The reaction was kept at 0° C. for an additional 15 minutes and stirred at room temperature for 3 hours. The methylene chloride was removed in vacuo. The residue was treated with hexane and the combined organic extract was concentrated in vacuo. The crude product was purified by flash chromatography on silica, eluting with straight hexane, to give 7.2 g (52%) of 11-bromoundecyne as a colorless oil. Following the procedures of Examples 20 and 39(a), a mixture of salicylaldehyde, 11-bromoundecyne and potassium carbonate in dimethylformamide is reacted to furnish 2-(10-undecynyloxy)benzaldehyde.

후처리

  1. customis reacted

출처 및 근거

ORD 기록
ord-42b36ef54d034d21a8378d05ae0d03bc
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04820719

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