Hydrochloric Acid → HCID 178465827, compound

HRID 1765011Notes

Reaction equation

HRID 1765011 reaction equation
[CH2:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[C:12]([F:21])[C:13]([F:20])=[C:14]([OH:19])[CH:15]=3)[O:10]2)[CH2:5][CH2:4]1)[CH3:2].I[CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[CH2:23]([O:19][C:14]1[CH:15]=[C:16]2[C:11](=[C:12]([F:21])[C:13]=1[F:20])[O:10][CH:9]([C@H:6]1[CH2:5][CH2:4][C@H:3]([CH2:1][CH3:2])[CH2:8][CH2:7]1)[CH2:18][CH2:17]2)[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178455703HCID 178455703, compound

Product 1

HCID 178465827HCID 178465827, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The DMF (100 ml) suspension containing 2-(trans-4-ethylcyclohexyl)-7,8-difluoro-6-hydroxychroman (28 g), iodoethane (25 g), and anhydrous potassium carbonate (15 g) was heated to reflux for 2 hours. The reaction solution was poured into 5% hydrochloric acid, extracted with toluene, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain 6-ethoxy-2-(trans-4-ethylcyclohexyl)-7,8-difluorochroman (30 g). Moreover, this was recrystallized using acetone to obtain 26 g of a pure substance.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with toluene
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-d1dbea5d375f4a60bc59dd042507e45b
Source dataset
uspto-grants-2007_06
Patent number
US07226644B2

Reaction notes

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