4-Toluenesulfonyl chloride → HCID 59504841、化合物

HRID 1496939ノート

反応式

HRID 1496939 の反応式
[F:1][C:2]1([F:8])[CH2:5][CH:4]([CH2:6][OH:7])[CH2:3]1.C(N(CC)CC)C.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl.O>[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:7][CH2:6][CH:4]2[CH2:5][C:2]([F:8])([F:1])[CH2:3]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

参加物

7

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 45480377(3,3-Difluorocyclobutyl)methanol

生成物 1

HCID 59504841HCID 59504841、化合物収率 97.3%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (3,3-difluorocyclobutyl)methanol (500 mg, 4.09 mmol, 1.00 equiv), triethylamine (662.6 mg, 6.55 mmol, 1.60 equiv), and 4-dimethylaminopyridine (750 mg, 6.14 mmol, 1.50 equiv) in CH2Cl2 (5 mL) under argon at 0° C. was added 4-methylbenzene-1-sulfonyl chloride (1.01 g, 5.30 mmol, 1.30 equiv) in portions. The resulting mixture was stirred overnight at ambient temperature. The mixture was then diluted with H2O (20 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were dried with anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified using flash column chromatography (silica gel, EtOAc/Hexanes (1:5)) to yield 1.1 g (97%) of a light yellow oil. 1H-NMR (300 MHz, CDCl3): δ ppm 7.77 (d, J=7.6 Hz, 2H), 7.34 (d, J=8.0 Hz, 2H), 4.03 (d, J=6.5 Hz, 2H), 2.75-2.50 (m, 2H), 2.50-2.36 (m, 4H), 2.36-2.08 (m, 2H).

後処理

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified

出典と根拠

ORDレコード
ord-da659c9cb2d34c1b834fbb5cc3f97ffc
出典データセット
uspto-grants-2015_12
特許番号
US09199945B2

反応ノート

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