Borane → [5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol

HRID 1028495

반응식

HRID 1028495 반응식
B.[CH:2]([C:5]1[CH:6]=[CH:7][C:8]([O:24][CH3:25])=[C:9]([C:11]2[C:12]([C:21](O)=[O:22])=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])[CH3:3].C(C1C=CC(OC)=C(C2C(C(N)=O)=CC(C(F)(F)F)=CC=2)C=1)(C)C>C1COCC1>[CH:2]([C:5]1[CH:6]=[CH:7][C:8]([O:24][CH3:25])=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][C:12]=2[CH2:21][OH:22])[CH:10]=1)([CH3:4])[CH3:3]

참가 물질

5

반응물 3

HCID 6331BoraneHCID 533636465'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-carboxylic acidHCID 667165875'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-carboxamide

생성물 1

HCID 53363647[5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of borane in THF (1 M, 859 μL, 0.859 mmol) was added dropwise to a stirred solution of 5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carboxylic acid and 5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carboxamide (3:1, 96.8 mg, 0.286 mmol) in dry THF at room temperature under N2. The reaction was stirred at room temperature for 3 h and carefully quenched with water (10 mL). The mixture was extracted with EtOAc (3×20 mL) and the combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 125×160 mm, 0-30% EtOAc in hexanes gradient) to afford [5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol as a colorless oil. Rf=0.27 (10% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 7.89 (br s, 1H), 7.62 (dd, J=8.0, 1.3 Hz, 1H), 7.36 (d, J=8.0 Hz, 1H), 7.29 (dd, J=8.5, 2.3 Hz, 1H), 7.03 (d, J=2.3 Hz, 1H), 6.96 (d, J=8.5, 1H), 4.51 (m, 2H), 3.74 (s, 3H), 2.93 (septet, J=7.0 Hz, 1H), 2.51 (s, 1H), 1.29 (d, J=7.0 Hz, 6H).

후처리

  1. customcarefully quenched with water (10 mL)
  2. extractionThe mixture was extracted with EtOAc (3×20 mL)
  3. washthe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThis was purified by flash chromatography (Si, 125×160 mm, 0-30% EtOAc in hexanes gradient)

출처 및 근거

ORD 기록
ord-e201db5433f14aa48d3192ab9897c227
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735435B2

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