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Potassium Carbonate → 2,3-dihydro-2,2-bis(pent-4-enyl)-8-propyl-7-[3-[(5,6,7,8-tetrahydro-1-naphthalenyl)oxy]propoxy]-4H-1-benzopyran-4-one

HRID 2371647
Notes
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Reaction equation

HRID 2371647 reaction equation
[CH2:1]([C:6]1([CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])[CH2:11][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][C:15]([OH:20])=[C:16]([CH2:17][CH2:18][CH3:19])[C:8]=2[O:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].[C:26]1([O:36][CH2:37][CH2:38][CH2:39]Br)[C:35]2[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=2[CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:21]([C:6]1([CH2:1][CH2:2][CH2:3][CH:4]=[CH2:5])[CH2:11][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][C:15]([O:20][CH2:39][CH2:38][CH2:37][O:36][C:26]3[C:35]4[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=4[CH:29]=[CH:28][CH:27]=3)=[C:16]([CH2:17][CH2:18][CH3:19])[C:8]=2[O:7]1)[CH2:22][CH2:23][CH:24]=[CH2:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 144059475-(3-Bromopropoxy)-1,2,3,4-tetrahydronaphthaleneHCID 151574722,3-dihydro-2,2-bis(pent-4-enyl)-8-propyl-7-hydroxy-4H-1-benzopyran-4-one

Product 1

HCID 151574732,3-dihydro-2,2-bis(pent-4-enyl)-8-propyl-7-[3-[(5,6,7,8-tetrahydro-1-naphthalenyl)oxy]propoxy]-4H-1-benzopyran-4-oneYield 82.7%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 3.0 g (9.55 mmol) of the title product of Example 69 and 4.01 g (11 mmol) of the title product of Example 12 in 56 ml of dry dimethylformamide (DMF) was added 2.77 g (20.1 mmol) of anhydrous potassium carbonate. The resulting mixture was stirred overnight at room temperature. The solvent was removed in vacuo, and the residue was partitioned between ethyl acetate and 3N hydrochloric acid. The aqueous layer was further extracted with two portions of ethyl acetate. The combined organic extracts were washed with water and with brine, dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure. Chromatography of the residue over silica gel, using 10% ethyl acetate/hexane as eluent, gave the title compound (4.19 g) as an oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and 3N hydrochloric acid
  3. extractionThe aqueous layer was further extracted with two portions of ethyl acetate
  4. washThe combined organic extracts were washed with water and with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7ea2eed87e164336a293e542615fd537
Source dataset
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05093353

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes