Hydrochloric Acid → (R)-(6-(benzyloxy)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl methanesulfonate

HRID 2365973ノート

反応式

HRID 2365973 の反応式
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]2[O:13][C@@H:14]([CH2:17][OH:18])[CH2:15][O:16][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].Cl>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]2[O:13][C@@H:14]([CH2:17][O:18][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:15][O:16][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66726995((S)-6-Benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol

生成物 1

HCID 86644715(R)-(6-(benzyloxy)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl methanesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of crude ((S)-6-benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol (1.65 g, 6.06 mmol) in dry DCM (10 ml), was added triethylamine (0.88 ml). The mixture was cooled to 0° C. and methanesulfonyl chloride (0.49 ml) was added slowly dropwise to reaction mixture. The mixture was stirred at RT for 1 h and then 10 ml of aq 1 M HCl was added. The mixture was extracted twice with DCM. The combined organic layers were washed with water and brine, dried with Na2SO4. The solvents were removed under reduced pressure and the crude product (2.22 g) was crystallized from IPA (15 ml), which gave a white solid (1.50 g).

後処理

  1. extractionThe mixture was extracted twice with DCM
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried with Na2SO4
  4. customThe solvents were removed under reduced pressure
  5. customthe crude product (2.22 g) was crystallized from IPA (15 ml), which

出典と根拠

ORDレコード
ord-43ad1762950548c6a8692eac2a48e0c1
出典データセット
uspto-grants-2014_04
特許番号
US08697723B2

反応ノート

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