Triethylamine → HCID 86601412, compound

HRID 854201Notes

Reaction equation

HRID 854201 reaction equation
[C:1]([O:4][CH:5]1[CH:6]([CH3:38])[CH2:7][CH2:8][CH:9]([OH:37])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:36])=[CH:20]/[CH:21]=[CH:22]/[C:23]([OH:35])([CH3:34])[CH2:24][CH:25]2[O:33][CH:26]2[CH:27]([CH3:32])[CH:28]([OH:31])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2].C(N([CH2:44][CH3:45])CC)C.[CH2:46]([Si:48](Cl)([CH2:51][CH3:52])[CH2:49][CH3:50])[CH3:47]>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:4][CH:5]1[CH:6]([CH3:38])[CH2:7][CH2:8][CH:9]([O:37][Si:48]([CH2:44][CH3:45])([CH2:49][CH3:50])[CH2:46][CH3:47])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:36])=[CH:20]/[CH:21]=[CH:22]/[C:23]([CH3:34])([O:35][Si:48]([CH2:51][CH3:52])([CH2:49][CH3:50])[CH2:46][CH3:47])[CH2:24][CH:25]2[O:33][CH:26]2[CH:27]([CH3:32])[CH:28]([O:31][Si:48]([CH2:51][CH3:52])([CH2:49][CH3:50])[CH2:46][CH3:47])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 13819ChlorotriethylsilaneHCID 11964536HCID 11964536, compound

Product 1

HCID 86601412HCID 86601412, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (8E,12E,14E)-7-acetoxy-3,16,21-trihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (54 mg, 0.1 mmol), 4-dimethylaminopyridine (124 mg, 1 mmol), and triethylamine (102 mg, 1 mmol) in methylene chloride (2.5 mL) was cooled to 5° C. A solution of triethylsilyl chloride (152 mg, 1 mmol) in methylene chloride (0.5 mL) was added dropwise to the reaction mixture, and then the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, and then the organic layer was washed with water. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane, 1:19->1:14) to obtain the title compound (77.1 mg, 88%) as a colorless oil.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane, 1:19->1:14)

Sources & evidence

ORD record
ord-2d45efe954c546a8b2d430f1d4ba4505
Source dataset
uspto-grants-2007_08
Patent number
US07256178B2

Reaction notes

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