Acetone → HCID 70378118, compound

HRID 1761795Notes

Reaction equation

HRID 1761795 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:38]=CC=1)/[CH:6]=[C:7]1\[CH2:8][C@@H:9]2[C@H:13]([CH2:14]\1)[C@H:12](/[CH:15]=[CH:16]/[C@@H:17]([O:24]C1CCCCO1)[CH:18]([CH3:23])[CH2:19][C:20]#[C:21][CH3:22])[C@H:11]([O:31]C1CCCCO1)[CH2:10]2)=O.[CH3:41][C:42]([CH3:44])=[O:43].O=[Cr](=O)=O.C1C=CC=CN=1.C1C=CC=CN=1.CCOCC>ClCCl>[C:42]([C:44]1[CH:38]=[C:5]([CH:4]=[CH:3][CH:1]=1)/[CH:6]=[C:7]1\[CH2:8][C@@H:9]2[C@H:13]([CH2:14]\1)[C@H:12](/[CH:15]=[CH:16]/[C@@H:17]([OH:24])[CH:18]([CH3:23])[CH2:19][C:20]#[C:21][CH3:22])[C@H:11]([OH:31])[CH2:10]2)(=[O:43])[CH3:41]

Participants

6

Reactant 4

HCID 180AcetoneHCID 3283Diethyl EtherHCID 88565Trioxobis(pyridine)chromiumHCID 131715941HCID 131715941, compound

Product 1

HCID 70378118HCID 70378118, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In order to convert the thus-obtained carbinol into the methyl ketone, the residue is dissolved in 50 ml of dichloromethane and this solution is added to 6 g of Collins reagent in 80 ml of dichloromethane. After 15 minutes, the mixture is combined with 300 ml of ether, filtered, and the filtrate washed in succession with water, 5% sodium bicarbonate solution, 10% strength sulfuric acid, and water, dried over magnesium sulfate, and evaporated under vacuum.

Workup

  1. filtrationfiltered
  2. washthe filtrate washed in succession with water, 5% sodium bicarbonate solution, 10% strength sulfuric acid, and water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-7a9089af96f64317a5168173b1b55767
Source dataset
uspto-grants-1989_05
Patent number
US04827017

Reaction notes

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