Dimethyl Sulfoxide → HCID 86644155, compound

HRID 534083Notes

Reaction equation

HRID 534083 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>ClCl.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

8

Reactant 4

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

Product 1

HCID 86644155HCID 86644155, compoundYield 110.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 24526ChlorineSolvent

Procedure

A solution of methylsulfinylmethane (20.6 ml, 289 mmol) in CH2 Cl2 (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]decane-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-3dccb769a1674022b867e491cacdae67
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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