HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium Carbonate → 6-Cyclopentyl-6-[2-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione

HRID 1438192
Notes
Print preview

Reaction equation

HRID 1438192 reaction equation
[CH:1]1([C:6]([OH:32])([CH2:17][CH2:18][C:19]2[CH:24]=[C:23]([CH2:25][CH3:26])[C:22]([OH:27])=[CH:21][C:20]=2[O:28][CH2:29][CH2:30][CH3:31])[CH2:7][C:8]2[O:13]C(C)(C)O[C:10](=[O:16])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]1([C:6]2([CH2:17][CH2:18][C:19]3[CH:24]=[C:23]([CH2:25][CH3:26])[C:22]([OH:27])=[CH:21][C:20]=3[O:28][CH2:29][CH2:30][CH3:31])[O:32][C:10](=[O:16])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 587640776-[2-Cyclopentyl-4-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-2-hydroxy-butyl]-2,2-dimethyl-[1,3]dioxin-4-one

Product 1

HCID 587641376-Cyclopentyl-6-[2-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dioneYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

6-[2-Cyclopentyl-4-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-2-hydroxy-butyl]-2,2-dimethyl-[1,3]dioxin-4-one (0.8 g, 1.8 mmol,) was dissolved in methanol (15 mL), treated with potassium carbonate (0.74 g, 5.4 mmol) and heated at 45° C. under N2 for 90 mins. The reaction mixture was partitioned between H2O and IPE. The aqueous layer was made acidic with 1N HCl and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to give the product as a yellow foam (0.5 g, 72% yield). 1H NMR (400 MHz, CDCl3): δ 1.02 (t, J=7.3 Hz, 3H), 1.19 (t, J=7.6 Hz, 3H), 1.41-1.87 (br m, 11H), 1.95 (m, 1H), 2.32 (m, 1H), 2.49-2.80 (m, 6H), 3.41 (m, 2H), 3.85 (m, 2H), 4.62 (s, 1H), 6.33 (s, 1H), 6.80 (s, 1H).

Workup

  1. customThe reaction mixture was partitioned between H2O and IPE
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-383342abfd6a4a3e9b4193a49cc96642
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07622605B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes