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Triethylamine → 2,2-dimethylpropionic acid 4-(4'-chloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethyl-5-oxo-5,6-dihydro-2H-pyran-3-yl ester

HRID 1470898
Notes
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Reaction equation

HRID 1470898 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[C:10]([CH:16]3[C:21](=[O:22])[C:20]([CH3:24])([CH3:23])[O:19][C:18]([CH3:26])([CH3:25])[C:17]3=[O:27])[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[C:10]([C:16]3[C:21](=[O:22])[C:20]([CH3:24])([CH3:23])[O:19][C:18]([CH3:26])([CH3:25])[C:17]=3[O:27][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[CH:9]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 684877684-(4'-Chloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione

Product 1

HCID 585157422,2-dimethylpropionic acid 4-(4'-chloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethyl-5-oxo-5,6-dihydro-2H-pyran-3-yl esterYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a solution of 4-(4′-chloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.077 g, 0.20 mmol) dissolved in anhydrous dichloromethane (3 ml) is added triethylamine (0.031 ml, 0.22 mmol) then pivaloyl chloride (0.027 ml, 0.22 mmol). This mixture is stirred at room temperature for 3 hours, then diluted with dichloromethane (15 ml) and washed with distilled water (2×10 ml). Organic fractions are combined, dried over magnesium sulphate, then concentrated to give a crude oil which is purified by flash chromatography (100% hexane to hexane/ethyl acetate 9:1 ratio) to afford 2,2-dimethylpropionic acid 4-(4′-chloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethyl-5-oxo-5,6-dihydro-2H-pyran-3-yl ester (0.090 g) as a colourless gum.

Workup

  1. washwashed with distilled water (2×10 ml)
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated
  4. customto give a crude oil which
  5. customis purified by flash chromatography (100% hexane to hexane/ethyl acetate 9:1 ratio)

Sources & evidence

ORD record
ord-a61e8b7de8e44a0287a1f6f634670d97
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09006429B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes