Triethylamine → HCID 57430948, compound

HRID 1866466Notes

Reaction equation

HRID 1866466 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:20][OH:21])[CH:8]=[C:9]([O:16][CH2:17][O:18][CH3:19])[C:10]=1[CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14].C(N(CC)CC)C.[Cl-].[S:30]([O-])(=[O:33])(=[O:32])[CH3:31]>C(Cl)Cl>[CH3:19][O:18][CH2:17][O:16][C:9]1[CH:8]=[C:7]([CH:6]=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:10]=1[CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH2:20][O:21][S:30]([CH3:31])(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16726324HCID 16726324, compoundHCID 21910748HCID 21910748, compound

Product 1

HCID 57430948HCID 57430948, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3,5-Bis-methoxymethoxy-4-(3-methyl-but-2-enyl)-phenyl]-methanol (2.0 g, 6.75 mmol) was dissolved in CH2Cl2 and placed in an ice bath. Triethylamine (1.2 ml, 8.92 mmol) was added and stirred until the reaction solution was at 0° C., followed by the dropwise addition of mesylate chloride (900 ul, 8.92 mmol). After stirring in the ice bath for 1 hour, the reaction was quenched with water, extracted with EtOAc, washed with brine, dried with MgSO4, filtered and evaporated yielding methanesulfonic acid 3,5-bis-methoxymethoxy-4-(3-methyl-but-2-enyl)-benzyl ester as a yellow oil. 1H NMR (CDCl3, 300 MHz) δ (ppm): 6.82 (s, 2H), 5.20 (t, 1H), 5.16 (s, 4H), 4.13 (s, 2H), 3.48 (s, 6H), 3.39 (d, 2H) 2.96 (s, 3H), 1.78 (s, 3H), 1.65 (s, 3H). MS (ESI) m/z: 375 (M+H)+, 397 (M+Na)+.

Workup

  1. customplaced in an ice bath
  2. customwas at 0° C.
  3. customthe reaction was quenched with water
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-3a3ccc51ef0e44898c5807d389b4387e
Source dataset
uspto-grants-2009_12
Patent number
US07629375B2

Reaction notes

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