Lithium borohydride → 2-(4,5-Difluoro-2,3-dihydro-1H-inden-1-yl)ethanol

HRID 1393295노트

반응식

HRID 1393295 반응식
C([O:3][C:4](=O)[CH2:5][CH:6]1[C:14]2[C:9](=[C:10]([F:16])[C:11]([F:15])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)C.[Li+].[BH4-]>CCOC(C)=O.C1COCC1.CO.[Pd]>[F:16][C:10]1[C:11]([F:15])=[CH:12][CH:13]=[C:14]2[C:9]=1[CH2:8][CH2:7][CH:6]2[CH2:5][CH2:4][OH:3]

참가 물질

7

반응물 2

HCID 4148881Lithium borohydrideHCID 66998529(4,5-Difluoro-indan-1-yl)-acetic acid ethyl ester

생성물 1

HCID 219860842-(4,5-Difluoro-2,3-dihydro-1H-inden-1-yl)ethanol

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of E- and Z-(4,5-difluoro-indan-1-ylidene)-acetic acid ethyl ester (Intermediate TWENTY-3) (1.1 g) in EtOAc (25 mL) was hydrogenated with 10% Pd/C (0.16 g) under H2 (balloon) at rt for 16 h. The mixture was filtered through a bed of Celite® and the filtrate was evaporated under vacuum. The ester, (4,5-difluoro-indan-1-yl)-acetic acid ethyl ester (1.1 g, 4.58 mmol) in THF (60 mL) and MeOH (1 mL) was treated with LiBH4 (0.21 g, 8.5 mmol) at 65° C. for 5 h. The mixture was cooled and THF was removed under vacuum. The solution was diluted with EtOAc and sat. NH4Cl. The layers were separated and the organic layer was dried over MgSO4 and filtered. After evaporation, the alcohol, 2-(4,5-difluoro-indan-1-yl)-ethanol (Intermediate TWENTY-4) was isolated as a clear, colorless oil, 1.7 g, (88%). Use, 2-(4,5-difluoro-indan-1-yl)-ethanol (Intermediate TWENTY-4) in Method SEVENTEEN produced 4-(4,5-difluoro-indan-1-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 156).

후처리

  1. filtrationThe mixture was filtered through a bed of Celite®
  2. customthe filtrate was evaporated under vacuum
  3. temperatureThe mixture was cooled
  4. customTHF was removed under vacuum
  5. additionThe solution was diluted with EtOAc and sat. NH4Cl
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customAfter evaporation

출처 및 근거

ORD 기록
ord-d68aeb72c767463787fa85bc1962de98
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07345077B2

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