Benzyl Chloride → HCID 86602616, compound

HRID 1366331Notes

Reaction equation

HRID 1366331 reaction equation
[CH2:1]([O:3][CH:4]([O:6][CH:7]1[CH2:19][CH2:18][C:17]([O:21][CH:22]([O:24][CH2:25][CH3:26])[CH3:23])([CH3:20])[CH:16]([OH:27])[CH:15]=[CH:14][CH:13]([CH3:28])[CH:12](/[C:29](/[CH3:56])=[CH:30]/[CH:31]=[CH:32]/[C:33]([O:50][CH:51]([O:53][CH2:54][CH3:55])[CH3:52])([CH3:49])[CH2:34][CH:35]2[O:48][CH:36]2[CH:37]([CH3:47])[CH:38]([O:41][CH:42]([O:44][CH2:45][CH3:46])[CH3:43])[CH2:39][CH3:40])[O:11][C:9](=[O:10])[CH2:8]1)[CH3:5])[CH3:2].[CH2:57](Cl)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1.C(OCC)(=[O:67])C>N1C=CC=CC=1>[C:57]([O:27][CH:16]1[C:17]([O:21][CH:22]([O:24][CH2:25][CH3:26])[CH3:23])([CH3:20])[CH2:18][CH2:19][CH:7]([O:6][CH:4]([O:3][CH2:1][CH3:2])[CH3:5])[CH2:8][C:9]([O:11][CH:12](/[C:29](/[CH3:56])=[CH:30]/[CH:31]=[CH:32]/[C:33]([O:50][CH:51]([O:53][CH2:54][CH3:55])[CH3:52])([CH3:49])[CH2:34][CH:35]2[O:48][CH:36]2[CH:37]([CH3:47])[CH:38]([O:41][CH:42]([O:44][CH2:45][CH3:46])[CH3:43])[CH2:39][CH3:40])[CH:13]([CH3:28])[CH:14]=[CH:15]1)=[O:10])(=[O:67])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8857Ethyl AcetateHCID 86602606HCID 86602606, compound

Product 1

HCID 86602616HCID 86602616, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (8E,12E,14E)-3,6,16,21-tetrakis(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (10 mg, 12.5 μmol) obtained in Example 3-2 in pyridine (0.5 mL) were added N,N-dimethylaminopyridine (8 mg, 62.5 μmol) and benzyl chloride (17.6 mg, 125 μmol) at room temperature, and the reaction mixture was stirred at the same temperature under nitrogen atmosphere for 12 hours. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous solution of ammonium chloride and brine. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 100 μm; ethyl acetate:hexane=25:75) to give the title compound (6 mg, 55%) as a colorless oil.

Workup

  1. washwashed with a saturated aqueous solution of ammonium chloride and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 100 μm; ethyl acetate:hexane=25:75)

Sources & evidence

ORD record
ord-26bb414bd9fc41b8ac934577e4c226e9
Source dataset
uspto-grants-2011_02
Patent number
US07893068B2

Reaction notes

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