Cesium carbonate → Methyl 6-methoxycarbonylmethoxy-2-naphthoate

HRID 23233

反応式

HRID 23233 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[CH:11]=2)[CH:6]=1)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>CC(C)=O.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:11]=2)[CH:6]=1)=[O:4]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 390995Methyl 6-hydroxy-2-naphthoate

生成物 1

HCID 18702924Methyl 6-methoxycarbonylmethoxy-2-naphthoate収率 85%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 6-hydroxy-2-naphthoic acid methyl ester (0.500 g, 2.47 mmol) in acetone (25 mL) at rt was added Cs2CO3 (0.886 g, 2.72 mmol) followed by methyl bromoacetate (0.257 mL, 2.72 mmol) dropwise. After 18 h at this temperature, it was diluted with EtOAc (200 mL). This layer was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL) and then dried (MgSO4). After concentration, the residue was recrystallized from MeOH:H2O to afford the product (0.573 g, 85%) as a solid; 1H NMR (DMSO-d6) δ3.71 (s, 3H), 3.87 (s, 3H), 4.95 (s, 2H), 7.30 (dd, J=2.6, 8.9 Hz, 1H), 7.38 (d, J=2.4 Hz, 1H), 7.87 (d, J=8.7 Hz, 1H), 7.92 (dd, J=1.6, 8.6 Hz, 1H), 8.06 (d, J=9.1 Hz, 1H), 8.55 (s, 1H); mass spectrum [(+) ESI], m/z 275 (M+H)+.

後処理

  1. washThis layer was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationAfter concentration
  4. customthe residue was recrystallized from MeOH

出典と根拠

ORDレコード
ord-afc1d9bee9814a05b930b7c13a07bb3f
出典データセット
uspto-grants-2005_02
特許番号
US06849761B2

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