Dimethyl Sulfate → HCID 13552532, compound

HRID 35428Notes

Reaction equation

[N:1]([C:4]([C:7]([C:10]([C:19]([F:22])([F:21])[F:20])([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[O:11][Na])([F:9])[F:8])([F:6])[F:5])=[N+:2]=[N-:3].S(OC)(O[CH3:27])(=O)=O>>[N:1]([C:4]([F:6])([F:5])[C:7]([F:9])([F:8])[C:10]([O:11][CH3:27])([C:19]([F:22])([F:21])[F:20])[O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[N+:2]=[N-:3]

Participants

Reactant 2

HCID 6497Dimethyl Sulfate

HCID 178514613HCID 178514613, compound

Product 1

HCID 13552532HCID 13552532, compoundYield 72%

Procedure

To demonstrate that the product was N3CF2CF2C(ONa)(OCH2CF3)CF3, the reaction mixture was stirred overnight with 56.7 g (0.45 mol) of dimethyl sulfate, then heated to 40° (0.5 mm, 0.1 kPa) to remove volatiles. Fractionation of the volatiles gave 101.4 g (72%) of 6-azido-4-methoxy-4-trifluoromethyl-1,1,1,5,5,6,6-hepta fluoro-3-oxahexane, bp 60°-61° (15 mm, 2.0 kPa). IR (CCl4): 3010, 2970, and 2660 (sat'd CH), 2150 (N3), 1300-1100 cm-1 (CF, C--O). NMR (CCl4): 1H 4.10 (q, JFF 7.8 Hz, 2H, CH2CF3) and 3.67 ppm (s, 3H, OCH3); 19F-73.8 (t of t, JFF 9.3, 7.9 Hz, 3F, CF3), -75.3 (t, JHF 7.8 Hz, 3F, CF3CH2), -89.3 (q or t, JFF 7.9, 3.4 Hz, 2F, CF2N3), and 117.7 ppm (q of t, JFF 9.3, 3.4 Hz, CF2).

Workup

temperatureheated to 40° (0.5 mm, 0.1 kPa)
customto remove volatiles

Sources & evidence

ORD record: ord-1e4b3ca37dd04352812da627d5128aa0
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04766248

Reaction notes

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