Triethylamine → HCID 86604547, compound

HRID 1446646Notes

Reaction equation

HRID 1446646 reaction equation
ClC(O[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=O.[CH2:14]([O:16][CH:17]([O:19][CH:20]1[CH2:32][CH2:31][C:30]([O:34][CH:35]([O:37][CH2:38][CH3:39])[CH3:36])([CH3:33])[CH:29]([OH:40])[CH:28]=[CH:27][CH:26]([CH3:41])[CH:25](/[C:42](/[CH3:63])=[CH:43]/[CH:44]=[CH:45]/[CH:46]([CH3:62])[CH2:47][CH:48]2[O:61][CH:49]2[CH:50]([CH3:60])[CH:51]([O:54][CH:55]([O:57][CH2:58][CH3:59])[CH3:56])[CH2:52][CH3:53])[O:24][C:22](=[O:23])[CH2:21]1)[CH3:18])[CH3:15].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:80](=O)([OH:82])[O-:81].[Na+]>ClCCl.O.C(OCC)(=O)C>[CH2:14]([O:16][CH:17]([O:19][CH:20]1[CH2:32][CH2:31][C:30]([O:34][CH:35]([O:37][CH2:38][CH3:39])[CH3:36])([CH3:33])[CH:29]([O:40][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[CH:28]=[CH:27][CH:26]([CH3:41])[CH:25](/[C:42](/[CH3:63])=[CH:43]/[CH:44]=[CH:45]/[CH:46]([CH3:62])[CH2:47][CH:48]2[O:61][CH:49]2[CH:50]([CH3:60])[CH:51]([O:54][CH:55]([O:57][CH2:58][CH3:59])[CH3:56])[CH2:52][CH3:53])[O:24][C:22](=[O:23])[CH:21]1[C:80]([OH:82])=[O:81])[CH3:18])[CH3:15]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 21023947(8E,12E,14E)-3,6,21-Tri(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide

Product 1

HCID 86604547HCID 86604547, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-nitrophenyl chloroformate (62 mg, 300 μmol) in dichloromethane (2.5 mL) was added dropwise into a solution of (8E,12E,14E)-3,6,21-tri(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (35 mg, 49.2 μmol), triethylamine (61 mg, 600 μmol) and dimethylaminopyridine (4 mg, 30 μmol) in dichloromethane (2.5 mL), followed by stirring at room temperature for 2.5 hours under nitrogen atmosphere. Ethyl acetate, water and saturated sodium bicarbonate aqueous solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate, then the organic layer was washed with water. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and then evaporated to give the title crude compound (92.2 mg) as a yellow oil. This was used for the following reaction without purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b4785036456d42debeffea309a35afb9
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

Loading…