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

HRID 494590노트

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HRID 494590 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
25 °C

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-e77b8d628f584b5c995b2c07c8cdb47f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538105B2

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