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

HRID 1180040

反応式

HRID 1180040 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-47bbc5c9258c42a59a954da5675c2c30
出典データセット
uspto-grants-2007_10
特許番号
US07279470B2

関連ノート

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