Methyl N-methylindole-6-carboxylate → (1-Methyl-1H-indol-6-yl)methanol

HRID 381319

반응식

HRID 381319 반응식
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)=O.BrC1C=C2C(C=CN2C)=CC=1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.O>[OH:2][CH2:3][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH3:14])=[CH:7][CH:6]=1

참가 물질

6

반응물 3

HCID 639843Methyl N-methylindole-6-carboxylateHCID 155468546-Bromo-1-methyl-1H-indoleHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 18673032(1-Methyl-1H-indol-6-yl)methanol

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 6-methoxycarbonyl-1-methylindole (prepared by the method of Example 1(b), but using 6-bromo-1-methylindole in place of 6-bromo-1-ethylindole, 5g) in tetrahydrofuran (30 ml) at −70° C. under a nitrogen atmosphere, was added diisobutyl aluminium hydride (66 ml of a 1.0M solution in tetrahydrofuran) dropwise with stirring. The solution was stirred at −70° C. for 15 mins then warmed to room temperature for 2 hours. The mixture was diluted with water (100 ml) and partitioned between ethyl acetate and aqueous sodium hydroxide. The aqueous layer was re-extracted with ethyl acetate and combined organic extracts were dried (MgSO4) and evaporated to give crude product which was purified by flash column chromatography using 80% ethyl acetate/20% hexane eluant to give the subtitle compound as a clear oil which solidified on standing (4.1 g).

후처리

  1. customat −70° C.
  2. stirringThe solution was stirred at −70° C. for 15 mins
  3. custompartitioned between ethyl acetate and aqueous sodium hydroxide
  4. extractionThe aqueous layer was re-extracted with ethyl acetate
  5. dry with materialwere dried (MgSO4)
  6. customevaporated
  7. customto give crude product which
  8. customwas purified by flash column chromatography

출처 및 근거

ORD 기록
ord-9ba638a6072b4b56b0c320b4d9763c87
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306852B1

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