Triphenylphosphine → HCID 86698865, compound

HRID 338549Notes

Reaction equation

[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.[CH3:17][C:18]1([CH2:22]O)[CH2:21][O:20][CH2:19]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:17][C:18]3([CH3:22])[CH2:21][O:20][CH2:19]3)=[CH:11][CH:10]=2)[O:5]1

Participants

Conditions

Temperature: 30 °C

Procedure

A vial was charged with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (220 mg, 1.00 mmol), (3-methyloxetan-3-yl)methanol (122 mg, 1.20 mmol), triphenylphosphine (353 mg, 1.50 mmol) and tetrahydrofuran (2 mL). The mixture was stirred at 30° C. for 15 min under nitrogen atmosphere. To the mixture was added Diisopropyl azodicarboxylate (300 mg, 1.50 mmol). The mixture was purged with nitrogen and heated to 50° C. for 17 hrs. The mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried (sodium sulfate) and concentrated to give crude product (900 mg) as yellow gum, which was purified through flash column chromatography to give the title compound (263 mg, 87%) as white solid.

Workup

customThe mixture was purged with nitrogen
temperatureheated to 50° C. for 17 hrs
additionThe mixture was diluted with ethyl acetate
washwashed with brine
dry with materialThe organic layer was dried (sodium sulfate)
concentrationconcentrated
customto give crude product (900 mg) as yellow gum, which
customwas purified through flash column chromatography

Sources & evidence

ORD record: ord-77e190acad084798b7def9fcb61f1f2a
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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