Formaldehyde → 6-Methoxy-3,4-dihydro-1H-2-benzopyran-1-one

HRID 1887545

반응식

HRID 1887545 반응식
[CH2:1]([Li])CCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[C:17]([CH3:24])[CH:16]=1.C=O>CCCCCC.C1COCC1.O>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:18](=[CH:22][CH:23]=1)[C:19](=[O:21])[O:20][CH2:1][CH2:24]2

참가 물질

8

반응물 4

HCID 712FormaldehydeHCID 7912DiisopropylamineHCID 5972164-Methoxy-2-methylbenzoic acidHCID 178418339Butyllithium

생성물 1

HCID 124011826-Methoxy-3,4-dihydro-1H-2-benzopyran-1-one

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

A 1.6M solution of n-butyllithium in hexane (145.9 mL) was added dropwise to a solution of diisopropylamine (33.5 mL) in dry THF (190 mL) at −78° C. The reaction mixture was then warmed to room temperature for 5 min and again cooled to −78° C., and a solution of 4-methoxy-2-methylbenzoic acid in dry THF (210 mL) was added dropwise. After stirring at this temperature for 10 min, paraformaldehyde (7 g) was added. The reaction mixture was then allowed to reach room temperature and was stirred at this temperature for 4 h. Water was added to the reaction mixture, and then the THF was removed in vacuo and the aqueous phase was extracted with diethyl ether. The aqueous phase was acidified with conc. HCl, and the resulting precipitate was filtered off and washed with water several times. The product with the molecular weight of 178.06 (C10H10O3) was obtained in this way; MS (ESI): 179 (M+H+).

후처리

  1. temperatureagain cooled to −78° C.
  2. customto reach room temperature
  3. stirringwas stirred at this temperature for 4 h
  4. customthe THF was removed in vacuo
  5. extractionthe aqueous phase was extracted with diethyl ether
  6. filtrationthe resulting precipitate was filtered off
  7. washwashed with water several times
  8. customThe product with the molecular weight of 178.06 (C10H10O3) was obtained in this way

출처 및 근거

ORD 기록
ord-e15a35bf3666477b9f2686c170eaecf4
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501771B2

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