Tetrahydrofuran → HCID 57705999, 화합물

HRID 2098918노트

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HRID 2098918 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[CH:18]([OH:23])[C:19]([CH3:21])([CH3:20])[CH3:22]

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 574675911-(2'-Fluoro-4-(hydroxymethyl)-5'-(methyloxy)-1,1'-biphenyl-2-yl)-2,2-dimethyl-1-propanone

생성물 1

HCID 57705999HCID 57705999, 화합물수율 75%

실험 절차

To a stirred solution of 1-(2′-fluoro-4-(hydroxymethyl)-5′-(methyloxy)-1,1′-biphenyl-2-yl)-2,2-dimethyl-1-propanone T9.6 (2.00 g, 6.3 mmol) in THF (63 mL, 6.3 mmol) at 0° C. was added LAH (1.0 M in THF, 13 mL, 13 mmol). Stirring was continued for 2 hours. 1N NaOH (aq) was added to the mixture, and the resulting mixture was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give the residue. The residue was purified by silica gel flash chromatography (0-30% EtOAc/hexane) to afford 1-(2′-fluoro-4-(hydroxymethyl)-5′-(methyloxy)-1,1′-biphenyl-2-yl)-2,2-dimethyl-1-propanol T9.7 (1.50 g, 75% yield) as a white solid. MS ESI (pos.) m/e: 336.2 (M+H2O)+. Chiral separation of T9.7 was accomplished on Chiracel-OD (4% IPA in hexane) to provide T9.8 and T9.9. Analytical column (Chiracel-OD (4% IPA in hexane, 45 min run) peak 1—18.5 mins, peak 2—24.5 mins).1

후처리

  1. extractionthe resulting mixture was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give the residue
  6. customThe residue was purified by silica gel flash chromatography (0-30% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-c2a3125ec8584504b8cc01bc16d4c101
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450522B2

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