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

HRID 38985

반응식

HRID 38985 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
140 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3377528d9b854baa9fa119b59dfddfc1
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524766B2

연결된 노트

불러오는 중…