Sulfuryl chloride → t-Butyl (carbonochloridoyloxy)methyl succinate

HRID 1397105Notes

Reaction equation

HRID 1397105 reaction equation
[C:1](=[O:19])(SCC)[O:2][CH2:3][O:4][C:5](=[O:15])[CH2:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].S(Cl)([Cl:23])(=O)=O>>[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])[CH2:7][CH2:6][C:5]([O:4][CH2:3][O:2][C:1]([Cl:23])=[O:19])=[O:15]

Participants

3

Reactant 2

HCID 24648Sulfuryl chloride2×HCID 86666520O-(3-(t-Butoxycarbonyl)propanoyloxy)methyl S-ethyl carbonothioate

Product 1

HCID 86666521t-Butyl (carbonochloridoyloxy)methyl succinate

Conditions

Temperature
0 °C

Procedure

To a solution of carbonothioate 2 (1.06 g, 3.63 mmol) in ice-cold CH2Cl2 (18 mL) was added sulfuryl chloride (441 μL, 5.44 mmol) and the mixture was stirred at 0° C. for 2 h 10 min, after which an additional amount of sulfuryl chloride (147 μL, 1.82 mmol) was added. The mixture was concentrated to dryness, providing chloroformate 3 as a colorless oil (1.13 g, >quant.) which was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 2.57-2.60 (m, 2H), 2.66-2.70 (m, 2H), 5.84 (s, 2H).

Workup

  1. concentrationThe mixture was concentrated to dryness

Sources & evidence

ORD record
ord-cde46642ee124ba493a6f2b838db1cc3
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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