Ethyl Acetate → methyl 5-formyl-(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-pentanecarboxylate

HRID 703682

Reaction equation

HRID 703682 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:14][CH2:15][CH:16]=C)[CH2:9][C:10](OC)=O.[O:18]=[O+][O-].[H][H].[C:23]([O:26][CH2:27]C)(=[O:25])C>>[CH:16]([CH2:15][CH2:14][C@@H:8]([O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:9][CH2:10][C:23]([O:26][CH3:27])=[O:25])=[O:18]

Participants

5

Reactant 4

HCID 8857Ethyl Acetate2×HCID 24823OzoneHCID 86743990methyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6-heptenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 86743989methyl 5-formyl-(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-pentanecarboxylate

Procedure

A solution of 2.56 g of methyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6-heptenoate in 40 ml of ethyl acetate is treated with ozone at -75° C. After the reaction has finished 0.1 g of Pd-on-carbon is added thereto and the mixture is hydrogenated at room temperature. After the hydrogen uptake has finished one filters off the catalyst, washes with ethyl acetate and evaporates in vacuo. There is obtained crude methyl 5-formyl-(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-pentanecarboxylate.

Workup

  1. additionis added
  2. customis hydrogenated at room temperature
  3. customevaporates in vacuo

Sources & evidence

ORD record
ord-5d9d0b90eb424adb83865c33781a2d11
Source dataset
uspto-grants-1991_01
Patent number
US04983746

Linked notes

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