Triethylamine → HCID 57485783, compound

HRID 749126Notes

Reaction equation

HRID 749126 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][CH:11]([CH2:13][OH:14])[CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4]1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([O:1][CH2:2][CH:3]1[CH2:12][CH:11]([CH2:13][O:14][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:10][C:5]2([O:6][CH2:7][CH2:8][O:9]2)[CH2:4]1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57485781HCID 57485781, compound

Product 1

HCID 57485783HCID 57485783, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7,9-bis(hydroxymethyl)-1,4-dioxaspiro[4.5]decane (6.3 g, 21 mmol) in dry dichloromethane (100 ml) with triethylamine (8.90 ml, 63.8 mmol) was added methanesulfonyl chloride (4.11 ml, 53.2 mmol) drop-wise at 0° C. The reaction was allowed to come to ambient temperature and stir overnight. The reaction was quenched with saturated sodium bicarbonate (50 ml) and allowed to stir for 15 min. After separation, the aqueous layer was extracted with dichloromethane (1×50 ml). The combined extracts were dried over potassium carbonate, filtered and concentrated to give a dark brown liquid (7.3 g, 97%).

Workup

  1. customto come to ambient temperature
  2. customThe reaction was quenched with saturated sodium bicarbonate (50 ml)
  3. stirringto stir for 15 min
  4. customAfter separation
  5. extractionthe aqueous layer was extracted with dichloromethane (1×50 ml)
  6. dry with materialThe combined extracts were dried over potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f563aeee4db34d0d90b37c199935be10
Source dataset
uspto-grants-2008_07
Patent number
US07402592B2

Reaction notes

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