Boron Trichloride → 7-hydroxy-3-(4-methoxyphenyl)-2H-1-benzopyran

HRID 254889ノート

反応式

HRID 254889 の反応式
C([O:8][C:9]1[CH:26]=[CH:25][C:12]2[CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH2:15][O:16][C:11]=2[CH:10]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[OH:8][C:9]1[CH:26]=[CH:25][C:12]2[CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH2:15][O:16][C:11]=2[CH:10]=1

参加物

4

反応物 2

HCID 25135Boron TrichlorideHCID 595921047-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran

生成物 1

HCID 98598477-hydroxy-3-(4-methoxyphenyl)-2H-1-benzopyran収率 81.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of compound 1 (0.2 g, 0.58 mmol) in dry CH2Cl2 (4 mL), a solution of BCl3 (1 M, 0.7 mL, 0.7 mmol) in CH2Cl2 was added dropwise at 0° C. under nitrogen. After stirring for 10 min, the mixture was quenched with ice water and a saturated NaHCO3 solution (10 mL), and then stirred for a further 20 min. After extraction with CH2Cl2 (15 mL×6), the organic layers were combined, washed with brine, and dried with anhydrous MgSO4. After filtration, the filtrate was concentrated in vacuo, followed by purification via silica gel column chromatography (ethyl acetate/n-hexane=1:4), thus giving the title compound 2b as a colorless crystal (0.12 g, 81% yield).

後処理

  1. customthe mixture was quenched with ice water
  2. stirringa saturated NaHCO3 solution (10 mL), and then stirred for a further 20 min
  3. extractionAfter extraction with CH2Cl2 (15 mL×6)
  4. washwashed with brine
  5. dry with materialdried with anhydrous MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customfollowed by purification via silica gel column chromatography (ethyl acetate/n-hexane=1:4)

出典と根拠

ORDレコード
ord-d1301a8728c140e49e52e2ee57fbce65
出典データセット
uspto-grants-2011_01
特許番号
US07875735B2

反応ノート

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