Potassium Carbonate → [7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

HRID 38985

反応式

HRID 38985 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([CH2:11][OH:12])[O:7][C:6]=2[CH:13]=1.[CH3:14][S:15]([O-:17])=[O:16].[Na+].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[CH3:14][S:15]([C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([CH2:11][OH:12])[O:7][C:6]=2[CH:13]=1)(=[O:17])=[O:16]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 233965(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanolHCID 2733271Sodium methanesulfinate

生成物 1

HCID 66878354[7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol収率 182.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
140 °C

実験手順

4 batches of a mixture of (7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl)methanol (0.5 g, 2.0 mmol), sodium methanesulfinate (85%) (0.37 g, 3.1 mmol), CuI (0.039 g, 0.2 mmol), L-proline (0.047 g, 0.4 mmol) and K2CO3 (0.056 g, 0.4 mmol) in DMSO (4 ml) was heated under microwave radiation to 140° C. for 1 h in a nitrogen-flushed vial. The batches were mixed and diluted with water and HCl (1 N). The resulting solution was extracted with EtOAc. The combined organic phases were washed with brine, dried and purified on flash column chromatography (isooctane/EtOAc/MeOH) to give the title compound (0.89 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (40), 165 (27), 134 (22), 79 (18).

後処理

  1. customflushed vial
  2. additionThe batches were mixed
  3. additiondiluted with water and HCl (1 N)
  4. extractionThe resulting solution was extracted with EtOAc
  5. washThe combined organic phases were washed with brine
  6. customdried
  7. custompurified on flash column chromatography (isooctane/EtOAc/MeOH)

出典と根拠

ORDレコード
ord-3377528d9b854baa9fa119b59dfddfc1
出典データセット
uspto-grants-2013_09
特許番号
US08524766B2

関連ノート

読み込み中…