Hydrochloric Acid → (1r)-1-(3,3-Dimethylbutyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one

HRID 2224910ノート

反応式

HRID 2224910 の反応式
[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][CH2:4][C@:5]1([CH3:22])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7](C(OCC)=O)[C:6]1=[O:21].Cl>O1CCOCC1>[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][CH2:4][C@:5]1([CH3:22])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[CH:7][C:6]1=[O:21]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 54740013Ethyl(4R)-4-(3,3-dimethylbutyl)-1-hydroxy-4-methyl-3-oxo-3,4-dihydronaphthalene-2-carboxylate

生成物 1

HCID 25260417(1r)-1-(3,3-Dimethylbutyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one収率 78.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
25 °C

実験手順

A solution of Example 49C (2.65 g, 8.02 mmol) in 1,4-dioxane (25 mL) was treated with aqueous 1 N hydrochloric acid solution (25 mL) and refluxed for 3 hours. The mixture was cooled to 25° C. and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water and brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was triturated in hot hexane and dried to give 1.62 g (61%) of the title compound. 1H NMR (300 MHz, CDCl3): δ ppm 0.43 m, 0.5 H) 0.83 m, 10 H) 1.06 (m, 0.5 H) 1.51 (s, 1.5 H) 1.56 (s, 1.5 H) 1.83 m, 1 H) 2.02 m, 0.5 H) 2.26 m, 0.5 H) 3.74 (s, 1 H) 6.09 (s, 0.5 H) 7.51 m, 3 H) 8.10 (td, J=7.81, 1.29 Hz, 1 H); MS (ESI−) m/z 257 (M−H)−.

後処理

  1. temperaturerefluxed for 3 hours
  2. custompartitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with water and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated in hot hexane
  8. customdried

出典と根拠

ORDレコード
ord-5f98be9bf7144eca8d7c0c5e7a167a1b
出典データセット
uspto-grants-2008_05
特許番号
US07378414B2

反応ノート

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