Hydrochloric Acid → Oxetan-3-ylmethyl 4-methylbenzene-1-sulfonate

HRID 878380ノート

反応式

HRID 878380 の反応式
[O:1]1[CH2:4][CH:3]([CH2:5][OH:6])[CH2:2]1.C(N(CC)CC)C.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:6][CH2:5][CH:3]2[CH2:4][O:1][CH2:2]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11521066Oxetan-3-ylmethanol

生成物 1

HCID 86670828Oxetan-3-ylmethyl 4-methylbenzene-1-sulfonate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of oxetan-3-yl-methanol (300 mg, 3.41 mmol, CAS RN 6246-06-6) in CH2Cl2 (3 mL) was added triethylamine (517 mg, 712 μl, 5.11 mmol), DMAP (41.6 mg, 341 μmol) and p-toluenesulfonyl chloride (779 mg, 4.09 mmol) at 0° C. The reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was poured on 30 mL 1M aqueous HCl and 30 mL CH2Cl2 and the layers were separated. The aqueous layer was extracted a second time with 30 mL CH2Cl2. The organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 50:50). Colorless liquid (595 mg, 72%).

後処理

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted a second time with 30 mL CH2Cl2
  3. washThe organic layers were washed with 30 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe compound was purified by silica gel chromatography on a 20 g column
  8. washeluting with a gradient of n-heptane:EtOAc (100:0 to 50:50)

出典と根拠

ORDレコード
ord-e3855d52c3ae452dab7c1e3b3a12dce3
出典データセット
uspto-grants-2015_03
特許番号
US08987307B2

反応ノート

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