Acetyl chloride → 3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoro-methyl)phenoxy)propan-1-ol

HRID 517984ノート

反応式

HRID 517984 の反応式
C(Cl)(=O)C.[CH3:5][C:6]1([CH3:34])[C:10]([CH3:12])([CH3:11])[O:9][B:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][O:23]C3CCCCO3)=[C:15]([C:30]([F:33])([F:32])[F:31])[CH:14]=2)[O:7]1>CO>[CH3:11][C:10]1([CH3:12])[C:6]([CH3:5])([CH3:34])[O:7][B:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][OH:23])=[C:15]([C:30]([F:32])([F:33])[F:31])[CH:14]=2)[O:9]1

参加物

4

反応物 2

HCID 6367Acetyl chlorideHCID 672941484,4,5,5-tetramethyl-2-(4-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy)-3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

生成物 1

HCID 672942723-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoro-methyl)phenoxy)propan-1-ol収率 101.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Acetyl chloride (14.26 ml) was added to MeOH (150 ml) at 0° C. and stirred for 10 minutes. The above mixture was added to 4,4,5,5-tetramethyl-2-(4-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy)-3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (43 g) in MeOH (300 ml) and stirred at 50° C. for 1.5 hours. The solvent was removed under reduced pressure, DCM was added to the residue and it was basified with sodium bicarbonate, washed with water, and the DCM was removed under reduced pressure to give expected compound (35 g). 1H NMR (CDCl3) δ: 8.00 (s, 1H), 7.92 (d, 1H), 6.98 (d, 1H), 4.21 (t, 2H), 3.86 (t, 2H), 2.07 (quin, 2H), 1.34 (s, 12H).

後処理

  1. stirringstirred at 50° C. for 1.5 hours
  2. customThe solvent was removed under reduced pressure, DCM
  3. additionwas added to the residue and it
  4. washwashed with water
  5. customthe DCM was removed under reduced pressure

出典と根拠

ORDレコード
ord-c4aea1c2fcc1428b86a8482c3c9b87ab
出典データセット
uspto-grants-2015_08
特許番号
US09115126B2

反応ノート

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