Dimethyl Sulfate → HCID 22452654、化合物

HRID 2185878ノート

反応式

HRID 2185878 の反応式
[I:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12]([OH:14])=[O:13])[C:3]=1O.S([O:21][CH3:22])(OC)(=O)=O.[C:23]([O-])([O-])=O.[K+].[K+].C(N(CC)CC)C>CC(C)=O>[I:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12]([O:14][CH3:23])=[O:13])[C:3]=1[O:21][CH3:22]

参加物

6

反応物 4

HCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 22452633HCID 22452633、化合物

生成物 1

HCID 22452654HCID 22452654、化合物収率 90%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a stirred suspension of 4-iodo-3-hydroxy-5,6,7,8-tetrahydro-2-naphthalenecarboxylic acid (23.43 g, 73.65 mmol) in dry acetone (450 mL) was added dimethyl sulfate (17.42 mL, 184.13 mmol) and K2CO3 (25.45 g, 184.13 mmol). The mixture was stirred at reflux overnight, cooled and triethylamine (40 mL) was added. After 0.5 h the mixture was filtered through a pad of diatomaceous earth and the filtrate concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL) and washed successively with 1N HCl (2×50 mL), sat. aqueous sodium bicarbonate (2×50 mL) and brine (50 mL ), dried (Na2SO4), filtered and concentrated in vacuo to afford a brown oil (22.52 g, 90%). 1H NMR (CDCl3) δ 7.56 (s, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 2.69 (m, 4H), 1.79 (m, 4H). MS m/z 347 (M+H).

後処理

  1. temperatureat reflux overnight
  2. temperaturecooled
  3. filtrationAfter 0.5 h the mixture was filtered through a pad of diatomaceous earth
  4. concentrationthe filtrate concentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  6. washwashed successively with 1N HCl (2×50 mL), sat. aqueous sodium bicarbonate (2×50 mL) and brine (50 mL )
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e74ef2ac30314ac28e255248793da22e
出典データセット
uspto-grants-2002_06
特許番号
US06403601B1

反応ノート

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