Water → trans-4-(4-Bromophenoxy)tetrahydrofuran-3-yl methanesulfonate

HRID 2060826Notes

Reaction equation

C(N(CC)CC)C.[Br:8][C:9]1[CH:21]=[CH:20][C:12]([O:13][C@@H:14]2[CH2:18][O:17][CH2:16][C@H:15]2[OH:19])=[CH:11][CH:10]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>C(Cl)Cl>[CH3:22][S:23]([O:19][C@H:15]1[C@H:14]([O:13][C:12]2[CH:20]=[CH:21][C:9]([Br:8])=[CH:10][CH:11]=2)[CH2:18][O:17][CH2:16]1)(=[O:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (181.9 mL, 1.31 mol) was added to a solution of trans-4-(4-bromophenoxy)tetrahydrofuran-3-ol from the previous step (354 g, assumed 300.6 g, 1.16 mol) in methylene chloride (2 L), and the reaction was cooled to 0° C. in an ice bath. Methanesulfonyl chloride (101.3 mL, 1.31 mol) was then added drop-wise, while keeping the reaction temperature below 5° C., and the reaction was stirred at room temperature for 18 hours. Water (1.5 L) was added, and the aqueous layer was extracted with methylene chloride. The organics were combined and dried over sodium sulfate, filtered and concentrated in vacuo to afford product as a brown oil. Yield: 399.6 g, 1.18 mol, quantitative. Material from a smaller-scale experiment carried out in similar fashion was triturated with ethanol for characterization. 1H NMR (400 MHz, CDCl3) δ 3.10 (s, 3H), 4.00 (br dd, J=10.4, 1.9 Hz, 1H), 4.07 (m, 1H), 4.16 (dd, J=11.1, 3.9 Hz, 1H), 4.23 (dd, J=10.5, 4.6 Hz, 1H), 4.98 (br d, J=4.6 Hz, 1H), 5.20 (m, 1H), 6.85 (d, J=9.1 Hz, 2H), 7.42 (d, J=9.0 Hz, 2H).

Workup

customthe reaction temperature below 5° C.
extractionthe aqueous layer was extracted with methylene chloride
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto afford product as a brown oil
customwas triturated with ethanol for characterization

Sources & evidence

ORD record: ord-8b67d65a1094436aa26e5ed05193a717
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278457B2

Reaction notes

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