Hydrochloric Acid → 1-(3-Methylthio-4-propoxy-5-benzyloxyphenyl)4-(3,4,5-trimethoxyphenyl)butan-1,4-dione

HRID 1110821ノート

反応式

HRID 1110821 の反応式
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[O:11][CH2:12][CH2:13][CH3:14])[CH:6]=[O:7].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:35]=[CH:36][C:37](C=CC2C=C(OC)C(OC)=C(OC)C=2)=O)[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32].C(N(CC)CC)C.Cl.CN(C)C=[O:64]>[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:6](=[O:7])[CH2:37][CH2:36][C:35]([C:27]2[CH:26]=[C:25]([O:24][CH3:23])[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=2)=[O:64])[CH:8]=[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[O:11][CH2:12][CH2:13][CH3:14]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 3834051,5-Bis(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-oneHCID 104710223-Methylthio4-n-propoxy-5-benzyloxybenzaldehyde

生成物 1

HCID 100987431-(3-Methylthio-4-propoxy-5-benzyloxyphenyl)4-(3,4,5-trimethoxyphenyl)butan-1,4-dione

試薬・触媒・溶媒 1

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide触媒

反応条件

温度
60 °C

実験手順

3-methylthio-4-n-propoxy-5-benzyloxybenzaldehyde, 135 g of 3,4,5-trimethoxyphenylvinylketone, 10 g of 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazoliumbromide, 25 mL of triethyl amine dissolved in 150 ml of dimethylformamide was heated at 60° C. overnight, and the reaction mixture was treated with 400 mL of 1.5N HCl and the aqueous layer decanted. The residue was treated again with fresh 400 mL of 1.5N HCl and decanted two more times. The remaining residue was crystallized from 400 mL of methanol and washed thoroughly with methanol, hexane, and methanol and dried to yield the title compound as a tan solid: NMR(200 MHz, CDCl3) δ 1.03(t, CH2CH2CH3), 1.82(m, CH2CH2CH3), 2.50(s, SCH3), 3.43(s, C(O)CH2CH2CO, 3.94(s, 3 OCH3), 4.11 (t, OCH2CH2CH3), 5.17(s, OCH2Ar), 7.30-7.52(m, ArH).

後処理

  1. customthe aqueous layer decanted
  2. additionThe residue was treated again with fresh 400 mL of 1.5N HCl
  3. customdecanted two more times
  4. customThe remaining residue was crystallized from 400 mL of methanol
  5. washwashed thoroughly with methanol, hexane, and methanol
  6. customdried

出典と根拠

ORDレコード
ord-5cac2286850a4cea96c3e94dde8153df
出典データセット
uspto-grants-1990_12
特許番号
US04977146

反応ノート

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