Potassium Iodide → Methyl 2-(4-Tert-Butyldimethylsilyloxymethyl-2-Allylphenoxy)-2-Phenylacetate

HRID 37224

反応式

HRID 37224 の反応式
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH2:17][CH:18]=[CH2:19])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1OCCOCCOCCOCCOCCOC1.Br[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[CH2:45][C:46]([O:48][CH3:49])=[O:47].[I-].[K+]>CN(C=O)C>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:45]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:39]=2)[C:46]([O:48][CH3:49])=[O:47])=[C:12]([CH2:17][CH:18]=[CH2:19])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 2855718-Crown-6HCID 8063364Methyl 2-(2-bromophenyl)acetateHCID 199348384-Tert-butyldimethylsilyloxymethyl-2-allylphenol

生成物 1

HCID 19934851Methyl 2-(4-Tert-Butyldimethylsilyloxymethyl-2-Allylphenoxy)-2-Phenylacetate収率 65.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

To a suspension of KH (1.3 eq) in DMF (1 mL) was added a solution of the product of Step C (157 mg, 0.566 mmol) in DMF (1 mL), followed by 18-crown-6 (30 mg; 0.2 eq). The reaction mixture was stirred for 5 minutes at room temperature. A solution of methyl 2-bromophenylacetate (168 mg, 0.735 mmol) in DMF (1 mL) was added, followed by a catalytic amount of potassium iodide. The reaction was heated to 80° C. for 0.5 hours then stirred at room temperature for 16 hours. After concentration in vacuo, the residue was partitioned between water and ethyl acetate. The combined organic layers were washed with water, brine, then dried (MgSO4). After filtration and concentration in vacuo, the residue was chromatographed on silica (MPLC, ethyl acetate/hexanes (5/95)) to afford 158 mg (66%) of the title compound (Rf =0.22, 5% ethyl acetate/hexanes).

後処理

  1. temperatureThe reaction was heated to 80° C. for 0.5 hours
  2. stirringthen stirred at room temperature for 16 hours
  3. concentrationAfter concentration in vacuo
  4. customthe residue was partitioned between water and ethyl acetate
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried (MgSO4)
  7. filtrationAfter filtration and concentration in vacuo
  8. customthe residue was chromatographed on silica (MPLC, ethyl acetate/hexanes (5/95))

出典と根拠

ORDレコード
ord-c0cc3718b5c04f88bf7fffa683d15765
出典データセット
uspto-grants-1995_05
特許番号
US05420133

関連ノート

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