Methanol → HCID 13118020, compound

HRID 2301804Notes

Reaction equation

HRID 2301804 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7]C(=C)[CH2:5][C@H:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O:15]=[O+][O-].CSC.[CH3:21][OH:22]>>[O:22]=[C:21]1[CH2:7][C@@H:3]([C:2]([OH:1])=[O:15])[C@H:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5]1

Participants

5

Reactant 4

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 24823OzoneHCID 18686190(+-)-trans-1-Hydroxymethyl-4-methylene-2-phenylcyclopentane

Product 1

HCID 13118020HCID 13118020, compound

Procedure

A solution of 1-(SR)-3-methylene-4-(SR)-phenylcyclopentanoic acid (84.8 g, 0.42 mol) from Example 20, Step B in methanol (2.5 L) was cooled to −70° C. in a dry-ice acetone bath. Ozone was bubbled through the solution until the blue color persisted. Excess ozone was removed with a stream of nitrogen and dimethyl sulfide (125 mL, 1.68 mol) was added. The mixture was then allowed to warm to rt over 16 h. Most of the methanol was removed in vacuo and the residue was taken up in ethyl acetate and washed twice with water and brine, dried over sodium sulfate and concentrated. The residue was triturated with hexanes and the solid was filtered and dried to afford the title compound (61.4 g).

Workup

  1. customOzone was bubbled through the solution until the blue color
  2. additionwas added
  3. customMost of the methanol was removed in vacuo
  4. washwashed twice with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was triturated with hexanes
  8. filtrationthe solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-5dc53d364dc34f468117954d14841651
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

Loading…