Tetrahydrofuran → Methyl 5-Acetoxy-2-bromomethyl-4-methoxyhydrocinnamate

HRID 1898764노트

반응식

HRID 1898764 반응식
[OH:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]([CH2:14]O[Si](C(C)(C)C)(C)C)=[C:6]([CH:13]=1)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].C1C[O:28][CH2:27][CH2:26]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:50]>CCOCC>[C:27]([O:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]([CH2:14][Br:50])=[C:6]([CH:13]=1)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])(=[O:28])[CH3:26]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 23372374Methyl 5-Hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

생성물 1

HCID 23372383Methyl 5-Acetoxy-2-bromomethyl-4-methoxyhydrocinnamate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of methyl 5-hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate (5.21 g) in carbon tetrabromide (12.35 g) in anhydrous ether (75 ml) and anhydrous THF (50 ml) is added portionwise triphenylphosphine (9.78 g) and the mixture stirred at room temperature for 60 minutes, diluted with ether, then filtered. The filtrate is concentrated in vacuo and the residue purified by filtration through silica gel in 50% ethyl acetate in hexanes followed by HPLC, eluting with 25% ethyl acetate in hexanes, to give the desired product.

후처리

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo
  3. filtrationthe residue purified by filtration through silica gel in 50% ethyl acetate in hexanes
  4. washeluting with 25% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-94763bb1c83c48a3b83869585f59d137
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05571506

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