Hydrochloric Acid → HCID 25109628, 화합물

HRID 1698411노트

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HRID 1698411 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]([OH:30])[C:17]#[C:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[C:21]([OH:29])[CH:20]=2)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].Cl>C1COCC1.CO>[C:1]([C:5]1[CH:6]=[C:7]([CH:16]([OH:30])[C:17]#[C:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[C:21]([OH:29])[CH:20]=2)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:3])([CH3:4])[CH3:2]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 67276336HCID 67276336, 화합물

생성물 1

HCID 25109628HCID 25109628, 화합물수율 44.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

1.7 g (4.3 mmol) of methyl 4-[3-(3-tert-butyl-4-diethylaminophenyl)-3-hydroxyprop-1-ynyl]-2-hydroxybenzoate are dissolved in 50 ml of THF with 1 ml of methanol and 2 ml of 1N aqueous NaCH. The solution is stirred at ambient temperature for 2 hours and then 2 days at reflux. The reaction medium is poured into a saturated solution of ammonium chloride, and the aqueous phase is brought to acidic pH with 1N HCl and then extracted twice with ethyl acetate. The organic phase is dried over magnesium sulphate and then concentrated to dryness. The residue is purified by chromatography (heptane/ethyl acetate: 50/50). 760 mg of 4-[3-(3-tert-butyl-4-diethylaminophenyl)-3-hydroxy-prop-1-ynyl]-2-hydroxybenzoic acid are obtained in the form of a whitish solid (Mp=245° C., yield=45%).

후처리

  1. temperature2 days at reflux
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated to dryness
  5. customThe residue is purified by chromatography (heptane/ethyl acetate: 50/50)

출처 및 근거

ORD 기록
ord-91c96eb8c6f843538932dab047e43779
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163952B2

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