Diiodomethane → 2-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 891951

反応式

HRID 891951 の反応式
[CH3:1][C:2]1([CH3:17])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[CH2:16])[CH:10]=2)[O:3]1.[CH2:18]([Zn]CC)C.ICI.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[CH:15]1([C:11]2[CH:10]=[C:9]([B:4]3[O:3][C:2]([CH3:17])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)[CH:14]=[CH:13][CH:12]=2)[CH2:18][CH2:16]1

参加物

6

反応物 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 222401702-(3-Ethenylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418750HCID 178418750、化合物

生成物 1

HCID 222402222-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane収率 69%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 4,4,5,5-tetramethyl-2-(3-vinyl-phenyl)-[1,3,2]dioxaborolane (300 mg, 1.3 mmol) in toluene (10 ml) were added diethylzinc solution (1.1 N in toluene, 5.22 ml, 5.74 mmol) and diiodomethane (8.7 ml, 33 mmol). The reaction mixture was stirred for 1 hour at room temperature and then refluxed for 3 hours. The reaction mixture was poured on sat. NH4Cl solution (20 ml) and was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide 2-(3-cyclopropyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (69% yield), 1H-NMR (300 MHz, CDCl3): δ=7.12-7.82 (m, 4H), 1.35 (s, 12H), 1.28 (t, 1H), 0.90-0.96 (m, 2H), 0.72-0.78 (m, 2H).

後処理

  1. temperaturerefluxed for 3 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-16faa739c8524138aadf0fb8526258e3
出典データセット
uspto-grants-2006_02
特許番号
US07005432B2

関連ノート

読み込み中…