Methyl Acetate → Methyl 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-3-hydroxypentanoate

HRID 1087589ノート

反応式

HRID 1087589 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:16][CH3:17])(=[O:15])[CH3:14].[CH3:18][C:19]([C:22]1[CH:23]=[C:24]([S:33][CH2:34][CH2:35][CH:36]=[O:37])[CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])([CH3:21])[CH3:20].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:32][C:29]([C:26]1[CH:25]=[C:24]([S:33][CH2:34][CH2:35][CH:36]([OH:37])[CH2:14][C:13]([O:16][CH3:17])=[O:15])[CH:23]=[C:22]([C:19]([CH3:18])([CH3:20])[CH3:21])[C:27]=1[OH:28])([CH3:30])[CH3:31]

参加物

8

反応物 5

HCID 6584Methyl AcetateHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 140118163-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanal2 回HCID 178418339Butyllithium

生成物 1

HCID 14390824Methyl 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-3-hydroxypentanoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 1.5 g of diisopropylamine in 25 ml of tetrahydrofuran (THF), stirred at -78° C. in an atmosphere of nitrogen, was added 6.5 ml of 1.6 M n-butyllithium in hexane. The mixture was stirred at -78° C. for 5 min after which a solution of 1.2 g of methyl acetate in 5 ml of THF was added. The mixture was again stirred at -78° C. for 5 min. Then a solution of 1.75 g of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanal, the product of Example 3, in 20 ml of THF was added. The reaction mixture was stirred at -78° C. for 1/2 hr. A saturated solution of ammonium chloride was carefully added, and the resultant mixture was allowed to warm to room temperature. The mixture was extracted with ether. The ether extract was washed with water, dried over anydrous MgSO4, and distilled to dryness under reduced pressure. The residual oil was chromatographed on silica gel. Elution with hexane-ethyl acetate followed by crystallization from aqueous methanol gave the product mp. 77°-80° C.

後処理

  1. additionwas added
  2. stirringThe reaction mixture was stirred at -78° C. for 1/2 hr
  3. temperatureto warm to room temperature
  4. extractionThe mixture was extracted with ether
  5. extractionThe ether extract
  6. washwas washed with water
  7. dry with materialdried over anydrous MgSO4
  8. distillationdistilled to dryness under reduced pressure
  9. customThe residual oil was chromatographed on silica gel
  10. washElution with hexane-ethyl acetate
  11. customfollowed by crystallization from aqueous methanol

出典と根拠

ORDレコード
ord-327f274c54ed464e817d45f2168c5a0b
出典データセット
uspto-grants-1991_07
特許番号
US05036105

反応ノート

読み込み中…