Triphenylphosphine → HCID 68576812, compound

HRID 273059Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:16]([N:29]1[CH2:32][CH:31]([CH2:33]O)[CH2:30]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[C:17]1([CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:29]2[CH2:32][CH:31]([CH2:33][O:1][C:2]3[CH:7]=[CH:6][C:5]([C:8]4([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)=[CH:4][CH:3]=3)[CH2:30]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 2758715(1-Benzhydrylazetidin-3-yl)methanol

HCID 5363146Diisopropyl azodicarboxylate

HCID 230916094-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile

Product 1

HCID 68576812HCID 68576812, compoundYield 41%

Procedure

4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (6.18 g, 30.4 mmol), (1-benzhydryl-azetidin-3-yl)-methanol (7 g, 28 mmol), PPh3 (8 g, 30.4 mmol), and DIAD (69 mL, 30.4 mmol), were reacted together similarly to general procedure C. The crude material was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate:diethylamine (50:45:5 to 0:95:5) to provide the title compound (5.03 g, 41%) as a yellow solid. LRMS APCI+ m/z 439 [MH]+.

Workup

customThe crude material was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate:diethylamine (50:45:5 to 0:95:5)

Sources & evidence

ORD record: ord-0d883d44d0d948f49b462a0f42631ff9
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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