Dichloromethane → HCID 59444759, compound

HRID 1160574Notes

Reaction equation

HRID 1160574 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.ClCCl.[Si:26]([O:33][CH:34]1[CH2:45][C:44](=[O:46])[O:43][C@H:42](/[C:47](/[CH3:51])=[CH:48]/[CH2:49][OH:50])[C@@H:41]([CH3:52])[CH:40]=[CH:39][C@@H:38]2[O:53][C@H:54]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[O:55][C@:37]2([CH3:62])[CH2:36][CH2:35]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CCOCC>[Si:26]([O:33][CH:34]1[CH2:45][C:44](=[O:46])[O:43][C@H:42](/[C:47](/[CH3:51])=[CH:48]/[CH:49]=[O:50])[C@@H:41]([CH3:52])[CH:40]=[CH:39][C@@H:38]2[O:53][C@H:54]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[O:55][C@:37]2([CH3:62])[CH2:36][CH2:35]1)([C:29]([CH3:30])([CH3:31])[CH3:32])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 66937743HCID 66937743, compound

Product 1

HCID 59444759HCID 59444759, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dess-Martin reagent (565 mg, 1.33 mmol) was added to a dichloromethane (12.0 ml) solution of (2S,3aS,4E,6S,7S,13aR)-11-{[tert-butyl(dimethyl)silyl]oxy}-7-{(1E)-3-hydroxy-1-methylprop-1-en-1-yl}-6,13a-dimethyl-2-phenyl-3a,6,7,10,11,12,13,13a-octahydro-9H-[1,3]dioxolo[4,5-f]oxacyclododecin-9-one (587 mg, 1.11 mmol). The reaction solution was stirred at room temperature for 30 minutes. The reaction solution was diluted with ether and washed with a saturated sodium hydrogen carbonate aqueous solution containing sodium sulfite, water and brine sequentially and dried over anhydrous magnesium sulfate. After 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 Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=10:1→8:1→6:1) to obtain the title compound (587 mg) as a white solid. This was obtained as a colorless crystal by recrystallization (hexane:ethyl acetate).

Workup

  1. washwashed with a saturated sodium hydrogen carbonate aqueous solution
  2. additioncontaining sodium sulfite, water and brine sequentially
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter the 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 Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=10:1→8:1→6:1)

Sources & evidence

ORD record
ord-78169459f72c4cc798a9f13e1f50ba6b
Source dataset
uspto-grants-2010_10
Patent number
US07816401B2

Reaction notes

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