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

HRID 1110821Notes

Reaction equation

HRID 1110821 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

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

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5cac2286850a4cea96c3e94dde8153df
Source dataset
uspto-grants-1990_12
Patent number
US04977146

Reaction notes

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