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

HRID 517984노트

반응식

HRID 517984 반응식
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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c4aea1c2fcc1428b86a8482c3c9b87ab
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115126B2

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