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

HRID 1898764ノート

反応式

HRID 1898764 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-94763bb1c83c48a3b83869585f59d137
出典データセット
uspto-grants-1996_11
特許番号
US05571506

反応ノート

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