Iodine → Ethyl 3-(2-iodo-5-methoxyphenyl)propionate

HRID 2044185ノート

反応式

HRID 2044185 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1.[I:16]I.C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC>C(#N)C>[I:16][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

参加物

5

反応物 3

HCID 807IodineHCID 159629ButyltriphenylphosphoniumHCID 584318Ethyl 3-(3-methoxyphenyl)propanoate

生成物 1

HCID 11110409Ethyl 3-(2-iodo-5-methoxyphenyl)propionate収率 76%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of ester 25 (1.618 g, 7.77 mmol) in acetonitrile (100 mL), iodine (1.972 g, 7.77 mmol) and n-butyltriphenylphosphonium peroxodisulfate (6.455 g, 7.77 mmol) were added and refluxed for 45 min. The reaction mixture was cooled to room temperature and the excess of iodine was removed by dropwise addition of 1M Na2S2O3 solution. The colourless solution was transferred to a separatory funnel and the organic layer was separated and dried over Na2SO4. Evaporation of the solvent followed by means of column chromatography on silica gel (hexane/isopropylether 10:1) gave 1.982 mg of iodinated ester 26 as a yellowish oil. Yield 76%. 1H NMR (300 MHz, CDCl3) δ ppm: 7.65 (d, J=8.7 Hz, 1H), 6.82 (d, J=3.0 Hz, 1H), 6.51 (dd, J1=8.7 Hz, J2=3.0 Hz, 1H), 4.14 (q, J=7.1 Hz, 2H), 3.76 (s, 3H), 3.00 (t, J=7.9 Hz, 2H), 2.60 (t, J=7.9 Hz, 2H), 1.25 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ ppm: 172.4, 160.0, 144.0, 139.9, 115.5, 114.1, 88.6, 60.5, 55.3, 35.9, 34.4, 14.2; HRMS (EI) m/z: calcd for C12H15|O3: 334.0065. found: 334.0082.

後処理

  1. temperaturerefluxed for 45 min
  2. customthe excess of iodine was removed by dropwise addition of 1M Na2S2O3 solution
  3. customThe colourless solution was transferred to a separatory funnel
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-1259d980fdb747048d72a771824451db
出典データセット
uspto-grants-2013_11
特許番号
US08586776B2

反応ノート

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