Methanol → HCID 11694680, compound

HRID 600747Notes

Reaction equation

HRID 600747 reaction equation
[CH2:1]([C:3]1([CH2:13][C:14]([C:16]([F:19])([F:18])[F:17])=C)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)[CH3:2].CSC.C[OH:24]>>[CH2:1]([C:3]1([CH2:13][C:14](=[O:24])[C:16]([F:19])([F:18])[F:17])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 116014351-Ethyl-1-[2-(trifluoromethyl)-2-propen-1-yl]-1,2,3,4-tetrahydronaphthalene2×

Product 1

HCID 11694680HCID 11694680, compoundYield 26%

Conditions

Temperature
-78 °C

Procedure

1-Ethyl-1-[2-(trifluoromethyl)-2-propen-1-yl]-1,2,3,4-tetrahydronaphthalene (Intermediate 12) (120 mg, 0.447 mmole) was dissolved in methanol (25 ml) and cooled to −78° C. Ozone was bubbled through the solution for 5 min followed by oxygen for 10 min then nitrogen for 10 min. Dimethyl sulphide (4 ml, 54 mmole) was added and the dry-ice bath was removed to bring the mixture to room temperature. Stirring was continued for 30 min then volatiles were removed in vacuo. The residue was purified on a 10 g silica SPE cartridge eluting with cyclohexane (200 ml), cyclohexane:ethyl acetate 80:20 (100 ml) and ethyl acetate (100 ml) to give the title compound (31 mg, 26%).

Workup

  1. customOzone was bubbled through the solution for 5 min
  2. waitnitrogen for 10 min
  3. customthe dry-ice bath was removed
  4. customto room temperature
  5. waitwas continued for 30 min
  6. customwere removed in vacuo
  7. customThe residue was purified on a 10 g silica SPE cartridge
  8. washeluting with cyclohexane (200 ml), cyclohexane:ethyl acetate 80:20 (100 ml) and ethyl acetate (100 ml)

Sources & evidence

ORD record
ord-fd96ac446f624c31bce9e7b293dcd413
Source dataset
uspto-grants-2011_03
Patent number
US07902224B2

Reaction notes

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