Triethylamine → HCID 86596993, compound

HRID 1727294Notes

Reaction equation

[Br:1][C:2]1[C:3](=O)[O:4][CH:5]([CH:9](O)[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[C:6]=1[O:7][CH3:8].C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl.CCOC(C)=O.O>[Br:1][C:2]1[CH2:3][O:4]/[C:5](=[CH:9]\[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)/[C:6]=1[O:7][CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-bromo-5-(hydroxynaphthalen-1-ylmethyl)-4-methoxy-5H-furan-2-one (5.3 g, 15.17 mmol) and triethylamine (9.22 g, 12.7 mL, 91.1 mmol) in anhydrous CH2Cl2 at 0° C. is treated dropwise with methane sulfonyl chloride (6.96 g, 4.7 mL, 60.7 mmol), stirred for 0.5 h at 0° C., allowed to warm to room temperature, treated sequentially with additional triethylamine (4.64 g, 6.4 mL, 45.9 mmol) and methane sulfonyl chloride (3.55 g, 2.4 mL, 31 mmol), stirred until the disappearance of starting material and diluted with EtOAc and water. The phases are separated and the organic phase is dried over Na2SO4 and concentrated in vacuo. The resultant residue is flash chromatographed (silica gel, 25% EtOAc in hexanes as eluent) to afford the title product as a yellow solid, 4.0 g (80% yield), mp 143-148° C., identified by NMR and mass spectral analyses.

Workup

temperatureto warm to room temperature
stirringstirred until the disappearance of starting material
customThe phases are separated
dry with materialthe organic phase is dried over Na2SO4
concentrationconcentrated in vacuo
customchromatographed (silica gel, 25% EtOAc in hexanes as eluent)

Sources & evidence

ORD record: ord-845edaa584db4b22b726aca43c3365d0
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495027B2

Reaction notes

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