Tetrahydrofuran → (2S)-2-ethyl-2-hydroxy-3-methyl-but-3-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

HRID 30494

反応式

HRID 30494 の反応式
[CH3:1][C@H:2]1[CH2:7][C@@H:6]([O:8][C:9](=[O:14])[C:10](=[O:13])[CH2:11][CH3:12])[C@H:5]([C:15]([CH3:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[CH2:4][CH2:3]1.[C:24]([Mg]Br)(C)=[CH2:25].O1CCC[CH2:30]1>>[CH3:1][C@H:2]1[CH2:7][C@@H:6]([O:8][C:9](=[O:14])[C@@:10]([CH2:24][CH3:25])([OH:13])[C:11]([CH3:30])=[CH2:12])[C@H:5]([C:15]([CH3:23])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH3:16])[CH2:4][CH2:3]1

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 110883962-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl esterHCID 178456138HCID 178456138、化合物

生成物 1

HCID 11530561(2S)-2-ethyl-2-hydroxy-3-methyl-but-3-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

実験手順

To a solution of 4.200 g of compound (17) as obtained from example 11 (13.27 mmol) in 168 mL tetrahydrofuran were added dropwise at −78° C. 39.8 mL isopropenylmagnesium bromide (19.91 mmol, 1.5 eq). After additional 50 min, the reaction mixture was quenched by addition of 110 mL saturated aqueous ammonium chloride solution, and was extracted twice with 110 mL ethyl acetate. The combined organic phases were washed with 110 mL brine, dried over 15 g sodium sulfate and were filtered. The filter cake was washed with 30 mL ethyl acetate. The organic phase was evaporated to dryness in a rotary evaporator (40° C., 8 mbar) yielding the title compound (4.790 g, 101% by weight, dr=93:7)as a yellow oil.

後処理

  1. additionwere added dropwise at −78° C
  2. customthe reaction mixture was quenched by addition of 110 mL saturated aqueous ammonium chloride solution
  3. extractionwas extracted twice with 110 mL ethyl acetate
  4. washThe combined organic phases were washed with 110 mL brine
  5. dry with materialdried over 15 g sodium sulfate
  6. filtrationwere filtered
  7. washThe filter cake was washed with 30 mL ethyl acetate
  8. customThe organic phase was evaporated to dryness in a rotary evaporator (40° C., 8 mbar)

出典と根拠

ORDレコード
ord-6fbe219456c14a61bdd0d9f0a5328882
出典データセット
uspto-grants-2008_09
特許番号
US07423152B2

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