Sodium Carbonate → HCID 10453585, compound

HRID 2248385Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].C([O-])([O-])=O.[Na+].[Na+].O[CH2:23][CH:24]1[O:28][C:27](=[O:29])[C:26]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:25]1>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][CH2:23][CH:24]1[O:28][C:27](=[O:29])[C:26]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:25]1)(=[O:5])=[O:4]

Participants

Conditions

Temperature: -40 °C

Procedure

Trifluoromethanesulfonic anhydride, 5.5 mL (32.5 mmol.), was added to 14 mL dry methylene chloride under argon at room temperature. The solution was cooled to -40° C. and 2.3 g (22 mmol.) of finely powdered, oven dried Na2CO3 was added. To the stirred mixture 6.7 g (25 mmol.) of 5-(hydroxymethyl)-4,5-dihydro-3,3-diphenyl-2(3H)furanone in 15 mL of methylene chloride was added dropwise, stirring 2 hours at -40° C. before warming to 0° C. for 0.5 hours. The reaction was quenched at 0° C. by adding 10 mL of water dropwise with vigorous stirring. The layers were separated, the organics washed with brine, dried (MgSO4), and evaporated at reduced pressure to a solid. This material was used as received and usually contained 5 to 15% of unreacted alcohol. 1H NMR (CDCl3)δ 2.77-2.83 (m, 1H), 3.05-3.14 (m, 1H), 4.51-4.71 (m, 2H), 4.7-4.75 (m, 1H), 7.25-7.45 (m, 10H).

Workup

temperaturebefore warming to 0° C. for 0.5 hours
customThe reaction was quenched at 0° C.
additionby adding 10 mL of water dropwise with vigorous stirring
customThe layers were separated
washthe organics washed with brine
dry with materialdried (MgSO4)
customevaporated at reduced pressure to a solid

Sources & evidence

ORD record: ord-fa9e516c50e04deaa971b25d7896113c
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05039691

Reaction notes

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