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

HRID 494590ノート

反応式

HRID 494590 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, 0.5H) 0.83 (m, 10H) 1.06 (m, 0.5H) 1.51 (s, 1.5H) 1.56 (s, 1.5H) 1.83 (m, 1H) 2.02 (m, 0.5H) 2.26 (m, 0.5H) 3.74 (s, 1H) 6.09 (s, 0.5H) 7.51 (m, 3H) 8.10 (td, J=7.81, 1.29 Hz, 1H); 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-e77b8d628f584b5c995b2c07c8cdb47f
出典データセット
uspto-grants-2009_05
特許番号
US07538105B2

反応ノート

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