4-Methoxybenzyl alcohol → (1-Hydroxy-5-methoxy-3-methyl-naphthalen-2-yl)-(4-methoxy-benzyloxy)-acetic acid ethyl ester

HRID 514037ノート

反応式

HRID 514037 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:21]([O:23][C:24](=[O:41])[CH:25]=[C:26]1[CH:35]([CH3:36])[CH:34](Br)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[O:38][CH3:39])[C:27]1=[O:40])[CH3:22]>C1COCC1>[CH2:21]([O:23][C:24](=[O:41])[CH:25]([C:26]1[C:35]([CH3:36])=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[O:38][CH3:39])[C:27]=1[OH:40])[O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:22]

参加物

5

反応物 3

HCID 77384-Methoxybenzyl alcoholHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86691540(4-bromo-5-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-naphthalen-2-ylidene)-acetic acid ethyl ester

生成物 1

HCID 67126070(1-Hydroxy-5-methoxy-3-methyl-naphthalen-2-yl)-(4-methoxy-benzyloxy)-acetic acid ethyl ester収率 68%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 4-methoxybenzyl alcohol (0.27 mL, 4 equiv) in THF (11 mL) at 0° C. was added KHMDS (0.5 M in toluene, 3.4 mL, 3 equiv) and the resulting mixture was allowed to stir for 10 min at 0° C. A solution of (4-bromo-5-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-naphthalen-2-ylidene)-acetic acid ethyl ester (200 mg) in THF (1 mL) was added slowly. After stirring for 3 min at 0° C., the reaction was quenched with citric acid (1 M) and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4 and concentrated. The crude residue was purified by flash column chromatography (5-20% EtOAc/hexanes) to give 157 mg of pale orange oil (68% yield). LCMS-ESI+ (m/z): [M+H]+ calcd for C24H27O6: 411.18. Found: 411.21.

後処理

  1. stirringAfter stirring for 3 min at 0° C.
  2. customthe reaction was quenched with citric acid (1 M)
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography (5-20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-903d7234fedb4984bb35bce9ab864c09
出典データセット
uspto-grants-2015_08
特許番号
US09102614B2

反応ノート

読み込み中…