(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 68153515, compound

HRID 1405400Notes

Reaction equation

HRID 1405400 reaction equation
O[C:2]([CH3:18])([CH3:17])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[O:15][CH3:16].COCCN(CCOC)S(F)(F)[F:25]>C(Cl)Cl>[F:25][C:2]([CH3:18])([CH3:17])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 68153566HCID 68153566, compound

Product 1

HCID 68153515HCID 68153515, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 4-(2-hydroxy-2-methyl-propoxy)-3-methoxy-benzoate (509 mg, 2.00 mmol) in DCM (5 mL) at 0° C. was added 2-methoxy-N-(2-methoxyethyl)-N-(trifluoro-sulfanyl)ethanamine (406 μL, 2.20 mmol) dropwise. The mixture was stirred at 0° C. for 1 h before the cooling bath was removed and the mixture was stirred for 1 h at room temperature. The mixture was poured into water and was extracted with EtOAc (3×). The organics were combined, washed with water, brine, dried (Na2SO4) and evaporated to dryness. Purification of the residue by column chromatography (0-20% EtOAc in Hex) gave methyl 4-(2-fluoro-2-methyl-propoxy)-3-methoxy-benzoate (450 mg, 70%). ESI-MS m/z calc. 256.1, found 257.1 (M+1)+; Retention time: 1.57 minutes (3 min run).

Workup

  1. customwas removed
  2. stirringthe mixture was stirred for 1 h at room temperature
  3. additionThe mixture was poured into water
  4. extractionwas extracted with EtOAc (3×)
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness
  8. customPurification of the residue by column chromatography (0-20% EtOAc in Hex)

Sources & evidence

ORD record
ord-3f26969b0010410fa5b87b4426a1d709
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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