Pivaloyl chloride → HCID 69945067, compound

HRID 2307529Notes

Reaction equation

HRID 2307529 reaction equation
[C:1]([O:9][CH2:10][C@H:11]1[S:15][CH2:14][C@H:13]([OH:16])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]([CH3:23])([CH3:22])[C:19](Cl)=[O:20]>ClCCl.N1C=CC=CC=1>[C:1]([O:9][CH2:10][C@H:11]1[S:15][CH2:14][C@H:13]([O:16][C:19](=[O:20])[C:18]([CH3:23])([CH3:22])[CH3:17])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 69435312HCID 69435312, compound

Product 1

HCID 69945067HCID 69945067, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of cis and trans 2-benzoyloxymethyl-5-hydroxy-1,3-oxathiolane (8.9 g, 39.6 mmol) (as prepared in example 1) was reacted with 14.6 mL (118.8 mmol) of trimethylacetylchloride in dichloromethane (35 mL) and pyridine (9.6 mL) as described in example 2 to yield 7.94 g of the desired compound in 1:1 ratio.

Sources & evidence

ORD record
ord-146181c178c54dc89a090c11205e71b4
Source dataset
uspto-grants-2004_12
Patent number
US06831174B2

Reaction notes

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