Triethylamine → HCID 58070838, compound

HRID 1193033Notes

Reaction equation

HRID 1193033 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]2[C:24](=[O:25])[CH:23]3[CH:18]([CH:19]4[CH2:27][CH2:26][CH:22]3[CH2:21][CH2:20]4)[C:17]2=[O:28])=[C:11]([CH3:29])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](Cl)(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32].C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH3:29])[C:12]([C:16]2[C:17](=[O:28])[CH:18]3[CH:23]([CH:22]4[CH2:26][CH2:27][CH:19]3[CH2:20][CH2:21]4)[C:24]=2[O:25][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 66709648HCID 66709648, compound

Product 1

HCID 58070838HCID 58070838, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-benzyloxy-2,6-dimethylphenyl)hexahydro-4,7-ethanoindene-1,3-dione (2.9 g, 0.008 mol), pivaloyl chloride (1.5 ml, 0.012 mol), triethylamine (2 ml, 0.0014 mol) and dichloromethane (100 ml) is stirred at room temperature for 3 hours. The reaction mixture is next evaporated and the crude product is dissolved in dichloromethane, absorbed on to silica then purified by flash column chromatography (20% ethyl acetate in hexanes as eluant) to afford 2,2-dimethylpropionic acid 2-(4-benzyloxy-2,6-dimethylphenyl)-3-oxo-3a,4,5,6,7,7a-hexahydro-3H-4,7-ethanoinden-1-yl ester.

Workup

  1. customThe reaction mixture is next evaporated
  2. dissolutionthe crude product is dissolved in dichloromethane
  3. customabsorbed on to silica
  4. customthen purified by flash column chromatography (20% ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record
ord-7759f9cc06534a37af296ceffd205c4a
Source dataset
uspto-grants-2014_03
Patent number
US08680339B2

Reaction notes

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