Methanesulfonyl chloride → HCID 86650639、化合物

HRID 1623392ノート

反応式

HRID 1623392 の反応式
[CH3:1][C:2]1([CH3:10])[O:7][CH:6]([CH2:8][OH:9])[CH2:5][O:4][CH2:3]1.[CH3:11][S:12](Cl)(=[O:14])=[O:13].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:11][S:12]([O:9][CH2:8][CH:6]1[CH2:5][O:4][CH2:3][C:2]([CH3:10])([CH3:1])[O:7]1)(=[O:14])=[O:13]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 66937181(6,6-Dimethyl-1,4-dioxan-2-yl)methanol

生成物 1

HCID 86650639HCID 86650639、化合物収率 98%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

TEA (0.52 mL, 3.74 mmol) and (6,6-dimethyl-1,4-dioxan-2-yl)methanol (390 mg, 2.67 mmol) were dissolved in DCM (10 mL). Methanesulfonyl chloride (0.249 mL, 3.20 mmol) was slowly added at 0° C. After the addition was completed the solution was warmed to ambient temperature and stirred for 1 hr. Saturated NaHCO3 solution was added and the two layers were separated. The aqueous layer was extracted three times with DCM. The organic layers were combined, dried over Na2SO4 and concentrated. The resulting residue was purified on a silica gel column (heptane:EtOAc 4:1 to 1:1) to give the product as a colorless oil (584 mg, 98%). 1H NMR (400 MHz, CDCl3) δ ppm 4.00-4.09 (3H, m), 3.74 (1H, dd, J=11.2, 2.8 Hz), 3.42 (1H, d, J=11.6 Hz), 3.16-3.23 (2H, m), 2.99 (3H, s), 1.27 (3H, s), 1.05 (3H, s).

後処理

  1. additionAfter the addition
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted three times with DCM
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified on a silica gel column (heptane:EtOAc 4:1 to 1:1)

出典と根拠

ORDレコード
ord-4758fe2eb511498a9540587c09ddb5fb
出典データセット
uspto-grants-2014_07
特許番号
US08778951B2

反応ノート

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