Dichloromethane → HCID 86618044, compound

HRID 1363850Notes

Reaction equation

HRID 1363850 reaction equation
C(N(CC)CC)C.Cl[Si:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:10][CH3:11].ClCCl.[C:19]([O:22][C@@H:23]1[C@@:34]([OH:36])([CH3:35])[CH2:33][CH2:32][C@@H:31]([OH:37])[CH2:30][C:29](=[O:38])[O:28][C@H:27](/[C:39](/[CH3:43])=[CH:40]/[CH:41]=[CH2:42])[C@@H:26]([CH3:44])[CH:25]=[CH:24]1)(=[O:21])[CH3:20]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:19]([O:22][C@@H:23]1[C@@:34]([OH:36])([CH3:35])[CH2:33][CH2:32][C@@H:31]([O:37][Si:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:10][CH3:11])[CH2:30][C:29](=[O:38])[O:28][C@H:27](/[C:39](/[CH3:43])=[CH:40]/[CH:41]=[CH2:42])[C@@H:26]([CH3:44])[CH:25]=[CH:24]1)(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 13819ChlorotriethylsilaneHCID 59444760HCID 59444760, compound

Product 1

HCID 86618044HCID 86618044, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (260 μl, 1.80 mmol), 4-dimethylaminopyridine (4.26 mg, 0.349 mmol) and chlorotriethylsilane (48 μl, 0.286 mmol) were added to an anhydrous dichloromethane (1.5 ml) solution of (2S,3S,4E,6S,7R,10R)-7,10-dihydroxy-3,7-dimethyl-2-[(1E)-1-methylbuta-1,3-dien-1-yl]-12-oxooxacyclododec-4-en-6-yl acetate (30.0 mg, 0.082 mmol) at room temperature and the reaction solution was stirred at the same temperature for five hours. The reaction solution was diluted with ethyl acetate and washed with a saturated sodium hydrogen carbonate aqueous solution, distilled water and brine. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto, commercial name Silica Gel 60N, 40-100 μm; heptane:ethyl acetate=1:2) to obtain the title compound (33 mg) as a white solid.

Workup

  1. washwashed with a saturated sodium hydrogen carbonate aqueous solution
  2. distillationdistilled water and brine
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  4. filtrationthe drying agent was filtered off
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (Kanto, commercial name Silica Gel 60N, 40-100 μm; heptane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-2921c7f1067348cfad02a6dbc8987e86
Source dataset
uspto-grants-2011_02
Patent number
US07884128B2

Reaction notes

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