Hydrochloric Acid → HCID 25109628、化合物

HRID 1698411ノート

反応式

HRID 1698411 の反応式
[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]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 67276336HCID 67276336、化合物

生成物 1

HCID 25109628HCID 25109628、化合物収率 44.7%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-91c96eb8c6f843538932dab047e43779
出典データセット
uspto-grants-2012_04
特許番号
US08163952B2

反応ノート

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