Isobutyric Acid → 2,2-Dimethyl-6-[2-[4-(4-morpholinyl)phenyl]ethoxy]hexanoic acid

HRID 1084960노트

반응식

HRID 1084960 반응식
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([OH:18])(=[O:17])[CH:14]([CH3:16])[CH3:15].Br[CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1>CCCCCC.C1COCC1>[CH3:15][C:14]([CH3:16])([CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1)[C:13]([OH:18])=[O:17]

참가 물질

7

반응물 4

HCID 6590Isobutyric AcidHCID 7912DiisopropylamineHCID 20062845HCID 20062845, 화합물HCID 178418339Butyllithium

생성물 1

HCID 200628192,2-Dimethyl-6-[2-[4-(4-morpholinyl)phenyl]ethoxy]hexanoic acid수율 99.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

n-Butyllithium in hexane (1.53M, 113.5 ml) was added dropwise to N,N-diisopropylamine (17.9 g) in THF (100 ml) at -78° under nitrogen. The mixture was warmed to 0°, stirred for 1 h and treated dropwise with isobutyric acid (7.65 g) in THF (20 ml). The resulting suspension was stirred at room temperature for 3 h, and the product of stage (ii) (20.0 g) was added dropwise. The reaction mixture was stirred for 16 h at room temperature and the solvent was evaporated. The resultant oil was partitioned between EA (250 ml) and water (250 ml). The aqueous layer was acidified to pH 6 with 2N aqueous hydrochloric acid and the organic extract was separated. The aqueous layer was extracted with EA (250 ml) and the combined extracts were concentrated to leave the title compound as an orange oil (20.4 g). T.l.c. (ER) Rf 0.53.

후처리

  1. temperatureThe mixture was warmed to 0°
  2. stirringThe resulting suspension was stirred at room temperature for 3 h
  3. stirringThe reaction mixture was stirred for 16 h at room temperature
  4. customthe solvent was evaporated
  5. customThe resultant oil was partitioned between EA (250 ml) and water (250 ml)
  6. extractionthe organic extract
  7. customwas separated
  8. extractionThe aqueous layer was extracted with EA (250 ml)
  9. concentrationthe combined extracts were concentrated

출처 및 근거

ORD 기록
ord-b66ede38bcb34ec8a39b0141e20bef09
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05006556

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