Hydrochloric Acid → HCID 71293089, 화합물

HRID 1404196노트

반응식

HRID 1404196 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:6][C:5]2=[O:19].O1CCCC1.B.Cl>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:6][CH:5]2[OH:19]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 71292849HCID 71292849, 화합물

생성물 1

HCID 71293089HCID 71293089, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-bromo-2-o-tolyl-chroman-4-one (11.0 g, 34.7 mmol) in tetrahydrofuran (100 ml) at room temperature a solution of borane tetrahydrofuran adduct (1M in tetrahydrofuran, 86.7 ml, 2.5 eq) was added dropwise. The solution was heated to reflux for 1 h, cooled to room temperature and added with caution to a mixture of ice water and 1N aqueous hydrochloric acid. The aqueous layer was extracted with dichloromethane, and the combined organic layers washed with water, dried with sodium sulfate and filtered and the solvent removed under reduced pressure. 6-Bromo-2-o-tolyl-chroman-4-ol was obtained as a yellow oil (11.1 g, 100%) and used in the reduction to the chroman without further purification.

후처리

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 h
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washthe combined organic layers washed with water
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-499cb36d9a214b11b7d6add458ef8536
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912224B2

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