Diethyl Ether → HCID 10539589, compound

HRID 376525Notes

Reaction equation

HRID 376525 reaction equation
[Br:1][C:2]1([CH2:13][OH:14])[C@@H:4]([C:5]([O:7][CH3:8])=[O:6])[C@@H:3]1[C:9]([O:11][CH3:12])=[O:10].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)C>ClCCl>[Br:1][C:2]1([CH:13]=[O:14])[C@@H:4]([C:5]([O:7][CH3:8])=[O:6])[C@@H:3]1[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10492026HCID 10492026, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 10539589HCID 10539589, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (1R,2R)-3-bromo-1,2-dicarbomethoxy-3-hydroxymethyl-cyclopropane (2.8 g, 10.5 mmol) in dichloromethane (120 ml) was added pyridinium chlorochromate (3.35 g, 15.7 mmol) and stirring continued over a period of 16 hours. Diethyl ether (120 ml) was added to the reaction mixture, which was then filtered with the aid of a Whatman glass microfibre filter and evaporated. Column chromatography of the crude product (diethyl ether/hexane 1:1) yielded (1R,2R)-3-bromo-1,2-dicarbomethoxy-3-formyl-cyclopropane (1.93 g, 69%) as a white solid. mp 52° C.; [α]20D=+108° (c=0.25 in MeOH): 1H NMR (CDCl3): d 3.16 (d, J=6.5 Hz, 1H), 3.27 (d, J=6.5 Hz, 1H), 3.76 (s, 3H), 3.83 (s. 3H), 9.26 (s, 1H). MS (EI) m/z 265, 267 [M+H+ ], 233, 235 (24) [M+ --OMe], 204, 206 (24), 176, 178 (44), 153 (100), 125 (95), 59 (69).

Workup

  1. filtrationwas then filtered with the aid of a Whatman glass microfibre
  2. filtrationfilter
  3. customevaporated

Sources & evidence

ORD record
ord-fc2fc9f3b3dd4cf99b4feb0d83c68602
Source dataset
uspto-grants-2000_02
Patent number
US06020525

Reaction notes

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