Triethylamine → HCID 12017363, compound

HRID 1937055Notes

Reaction equation

HRID 1937055 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7]/[C:8](/[CH3:16])=[CH:9]/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH2:14][OH:15].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7]/[C:8](/[CH3:16])=[CH:9]/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH2:14][O:15][S:25]([CH3:24])(=[O:27])=[O:26]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12017361HCID 12017361, compound

Product 1

HCID 12017363HCID 12017363, compoundYield 89%

Procedure

Methanesulfonic acid (4E,6E)-9-[1,3]dioxolan-2-yl-7-methyl-nona-4,6-dienyl ester was synthesized using the following procedure. To a cooled (0° C.) solution of (4E,6E)-9-[1,3]dioxolan-2-yl-7-methyl-nona-4,6-dien-1-ol (1.60 g, 7.20 mmol), triethylamine (1.2 mL, 8.6 mmol), and 15 mL of CH2CI2 was added dropwise methanesulfonyl chloride (0.61 mL, 7.9 mmol). The reaction mixture was stirred at 0° C. to room temperature for 2.5 h, quenched with a saturated NaHCO3 solution, extracted with EtOAc, dried (Na2SO4), and concentrated to give 1.95 g (6.41 mmol, 89%) of methanesulfonic acid (4E,6E)-9-[1,3]dioxolan-2-yl-7-methyl-nona-4,6-dienyl ester which was used without further purification: 1H NMR δ6.28 (dd, 1H, J-15.0, 10.9 Hz), 5.82 (d, 1H,J-10.7 Hz), 5.52 (dt, 1H,J-15.0, 7.0 Hz), 4.85 (t, 1H,J-4.8 Hz), 4.23 (t, 2H, J-6.4 Hz), 4.00-3.75 (m, 4H), 3.00 (s, 3H), 2.25-2.12 (m, 4H), 1.90-1.75 (m, 4H), 1.74 (s, 3H).

Workup

  1. customMethanesulfonic acid (4E,6E)-9-[1,3]dioxolan-2-yl-7-methyl-nona-4,6-dienyl ester was synthesized
  2. customquenched with a saturated NaHCO3 solution
  3. extractionextracted with EtOAc
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ae82bfc2bf9940b3916c55241989a81d
Source dataset
uspto-grants-2002_05
Patent number
US06392055B1

Reaction notes

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