Benzoyl chloride → HCID 21024031, compound

HRID 1446642Notes

Reaction equation

HRID 1446642 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:11]([O:13][CH:14]([O:16][CH:17]1[CH2:29][CH2:28][C:27]([O:31][CH:32]([O:34][CH2:35][CH3:36])[CH3:33])([CH3:30])[CH:26]([OH:37])[CH:25]=[CH:24][CH:23]([CH3:38])[CH:22](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([O:51][CH:52]([O:54][CH2:55][CH3:56])[CH3:53])[CH2:49][CH3:50])[O:21][C:19](=[O:20])[CH2:18]1)[CH3:15])[CH3:12].[C:61](Cl)(=[O:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1.C(OCC)(=O)C>O1CCCC1.O>[C:61]([O:37][CH:26]1[C:27]([O:31][CH:32]([O:34][CH2:35][CH3:36])[CH3:33])([CH3:30])[CH2:28][CH2:29][CH:17]([O:16][CH:14]([O:13][CH2:11][CH3:12])[CH3:15])[CH2:18][C:19]([O:21][CH:22](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([O:51][CH:52]([O:54][CH2:55][CH3:56])[CH3:53])[CH2:49][CH3:50])[CH:23]([CH3:38])[CH:24]=[CH:25]1)=[O:20])(=[O:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 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 21024031HCID 21024031, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

LiHMDS (1.0 M tetrahydrofuran solution, 81 μL, 81 μmol) was added dropwise to 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 (10 mg, 14 μmol) in tetrahydrofuran (1 mL) at −40° C. under nitrogen atmosphere. After stirring at the same temperature for 15 min., a solution of benzoyl chloride (17.8 mg, 125 μmol) in tetrahydrofuran (0.4 mL) was added dropwise thereto and the mixture was stirred at 0° C. for 7 hours. Ethyl acetate and water were added to the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane=1:4) to obtain the title compound (6.1 mg, 54%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at 0° C. for 7 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane=1:4)

Sources & evidence

ORD record
ord-ef66017533bb4d4abf408bc8247c143b
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

Loading…