Triethylamine → HCID 57567186, compound

HRID 1445947Notes

Reaction equation

[Br:1][C:2]1[C:3](=[O:21])[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[C:3](=[O:21])[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 143-1481° 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-45131cd41f88473f95b93b4587d8f8f8
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666904B2

Reaction notes

Loading…