Hydrochloric Acid → HCID 68537270、化合物

HRID 1992866ノート

反応式

HRID 1992866 の反応式
[CH3:1][CH:2]([C:4]1[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([O:16]COC)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH3:3].Cl>O1CCOCC1.O.[Cl-].[Na+].O>[CH3:3][CH:2]([C:4]1[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([OH:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH3:1]

参加物

6

反応物 2

HCID 313Hydrochloric AcidHCID 68539388HCID 68539388、化合物

生成物 1

HCID 68537270HCID 68537270、化合物収率 99.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

3-(1-Methylethyl)-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-phenyl naphthalene (71) (0.42 g, 1.24 mmol) was dissolved in dioxane (8 mL). 4 M HCl in dioxane (8 mL) was added and the reaction mixture was stirred at room temperature for 30 min. The mixture was diluted with water (25 mL) and brine (25 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a light yellow oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (20:1) to give 0.36 g (98%) of the title compound (72) as a white solid. 1H NMR (400 MHz, CDCl3): δ 1.16 (d, J=6.8 Hz, 6H), 2.79 (sept, J=6.8 Hz, 1H), 3.93 (s, 3H), 5.08 (s, 1H), 7.05-7.12 (m, 2H), 7.30 (s, 1H), 7.32-7.38 (m, 2H), 7.42-7.50 (m, 1H), 7.50-7.58 (m, 2H), 8.07 (d, J=9.0 Hz, 1H). LCMS (APCI): m/z 293 (M+H)+.

後処理

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customto give the crude product as a light yellow oil
  7. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (20:1)

出典と根拠

ORDレコード
ord-6db98b2e20b54d01a3ab8564f16b018a
出典データセット
uspto-grants-2010_01
特許番号
US07649093B2

反応ノート

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