Dimethyl Sulfoxide → HCID 86644155, compound

HRID 1523640Notes

Reaction equation

HRID 1523640 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][CH2:13][C@@H:14]1[O:18][C:17]2([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[O:16][C@H:15]1[CH2:24][OH:25].C(N(CC)CC)C>C(Cl)Cl.O>[CH3:11][O:12][CH2:13][C@@H:14]1[O:18][C:17]2([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[O:16][C@H:15]1[CH:24]=[O:25]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67486253HCID 67486253, compound

Product 1

HCID 86644155HCID 86644155, compoundYield 110.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of methylsulfinylmethane (20.6 ml, 289 mmol) in CH2Cl2 (260 mL) at −60° C., was added dropwise to a 2M solution of oxalyl dichloride (15.2 ml, 174 mmol) in CH2Cl2 (80 mL). The mixture was stirred for 20 minutes and then a solution of ((2S,3S)-3-(methoxymethyl)-1,4-dioxaspiro[4.5]decan-2-yl)methanol (31.3 g, 145 mmol) in CH2Cl2 (80 mL) was added dropwise. The mixture was stirred for 10 minutes and then triethylamine (101 ml, 724 mmol) was slowly added. The reaction mixture was warmed to ambient temperature and water was added. When the mixture became clear, it was extracted with CH2Cl2, dried over sodium sulfate, filtered and concentrated to afford crude (2R,3S)-3-(methoxymethyl)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde (34.3 g, 96.2% yield, 87% pure) which was taken on to next reaction without further purification.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. extractionit was extracted with CH2Cl2
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-66fb9bf743af41e99e671c60ca655bdf
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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