Trifluoroacetic acid → 4-(2-Fluorobenzyl)cyclohexanecarboxylic Acid Methyl Ester

HRID 1015362

反応式

HRID 1015362 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11](=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH2:7][CH2:6]1)=[O:4].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[CH3:1][O:2][C:3]([CH:5]1[CH2:6][CH2:7][CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH2:9][CH2:10]1)=[O:4]

参加物

4

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 575168734-(2-Fluorobenzoyl)cyclohexanecarboxylic Acid Methyl Ester

生成物 1

HCID 673020364-(2-Fluorobenzyl)cyclohexanecarboxylic Acid Methyl Ester収率 83.2%

実験手順

In an 18 mL vial with stir bar and 4-(2-fluorobenzoyl)cyclohexanecarboxylic acid methyl ester (333 mg; 1.2 mmol), trifluoroacetic acid (4 mL) was chilled to 0° C. and triethylsilane (700 mg; 6.0 mmol) was added over 1 minute. Mixture was allowed to warm to room temperature. After 48 hours, mixture was concentrated in vacuo and reduced by half volume. Mixture was poured into cold KOH solution and pH adjust further to pH 6. Aqueous mixture was extracted 3×5 mL ethyl acetate. Combined ethyl acetate was washed with brine and dried over MgSO4. Crude oil was purified via (20:1) flash chromatography 0-10% ethyl acetate in hexanes to give 250 mg of title compound. (83% yield).

後処理

  1. concentrationmixture was concentrated in vacuo
  2. additionMixture was poured into cold KOH solution
  3. extractionAqueous mixture was extracted 3×5 mL ethyl acetate
  4. washCombined ethyl acetate was washed with brine
  5. dry with materialdried over MgSO4
  6. customCrude oil was purified via (20:1) flash chromatography 0-10% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-eb8677f7660f4a8b9165adf123a9adfd
出典データセット
uspto-grants-2011_07
特許番号
US07985755B2

関連ノート

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