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

HRID 1196693

반응식

HRID 1196693 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide촉매

반응 조건

온도
60 °C

실험 절차

175 g 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 l 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).

후처리

  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

출처 및 근거

ORD 기록
ord-e6f29986101b474eab83a70a70d679fc
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05114961

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