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

HRID 1913833노트

반응식

HRID 1913833 반응식
[CH:1](NC(C)C)(C)C.C([Li])CCC.[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>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

7

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 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of diisopropylamine (33.5 ml) in dry THF (190 ml) was added dropwise, at −78° C., n-butyllithium (1.6 M solution in hexane, 145.9 ml). Subsequently, the reaction mixture was warmed to room temperature for 5 minutes and then cooled again to −78° C., and a solution of 4-methoxy-2-methylbenzoic acid (10 g) in dry THF (210 ml) was added dropwise. After stirring at this temperature for 10 minutes, paraformaldehyde (7 g) was added. The reaction mixture was then allowed to come to room temperature and stirred at this temperature for 4 hours. The reaction mixture was admixed with water, then the THF was removed under reduced pressure and then 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 repeatedly with water. The product was thus obtained with the molecular weight of 178.06 (C10H10O3); MS (ESI): 179 (M+H+).

후처리

  1. temperaturecooled again to −78° C.
  2. customto come to room temperature
  3. stirringstirred at this temperature for 4 hours
  4. customthe THF was removed under reduced pressure
  5. extractionthe aqueous phase was extracted with diethyl ether
  6. filtrationthe resulting precipitate was filtered off
  7. washwashed repeatedly with water
  8. customThe product was thus obtained with the molecular weight of 178.06 (C10H10O3)

출처 및 근거

ORD 기록
ord-cdb9bb6afbfa437d8f42d7b851829380
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609731B2

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