Trifluoroacetic acid → 4-[4-(2-Pyrrolidin-1-yl-ethoxy)-benzyl]-phenol

HRID 1180040

반응식

HRID 1180040 반응식
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C[Si](C)(C)[O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C1COCC1.C(Cl)Cl>[N:9]1([CH2:8][CH2:7][O:6][C:5]2[CH:14]=[CH:15][C:2]([CH2:23][C:22]3[CH:25]=[CH:26][C:19]([OH:18])=[CH:20][CH:21]=3)=[CH:3][CH:4]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 70536p-((Trimethylsilyl)oxy)benzaldehydeHCID 70657N-(2-(p-bromophenoxy)ethyl)pyrrolidine

생성물 1

HCID 220479654-[4-(2-Pyrrolidin-1-yl-ethoxy)-benzyl]-phenol수율 94.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 1-[2-(4-bromo-phenoxy)-ethyl]-pyrrolidine (2.89 g, 10.7 mmol) in THF (30 mL) was added dropwise 1.6 M solution in hexanes n-BuLi (7 mL, 10.2 mmol) over a 5-min period at −78° C. The mixture was stirred at −78° C. for 15 min before 4-trimethylsilyloxybenzaldehyde (2.08 g, 10.7 mmol) was added. The mixture was allowed to warm to rt during 20 min and quenched with water. Extraction with CH2Cl2, drying (MgSO4), filtration and evaporation provided the crude diarylmethanol which was dissolved in CH2Cl2 (30 mL) and stirred with triethylsilane (4 mL) and TFA (5 mL) for 16 h at rt. Evaporation gave 3.0 g (84%) 4-[4-(2-pyrrolidin-1-yl-ethoxy)-benzyl]-phenol. This was carbamoylated using general procedure 1 (CH2Cl2 was used as solvent) to give the title product after purification by preparative HPLC (Gilson) (35%, oil).

후처리

  1. additionwas added
  2. customquenched with water
  3. extractionExtraction with CH2Cl2
  4. customdrying
  5. filtration(MgSO4), filtration and evaporation
  6. customprovided the crude diarylmethanol which
  7. customEvaporation

출처 및 근거

ORD 기록
ord-47bbc5c9258c42a59a954da5675c2c30
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279470B2

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