Triphenylphosphine → 4-(4-tert-butoxyphenoxy)tetrahydro-2H-pyran

HRID 513182Notes

Reaction equation

HRID 513182 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[O:32]1[CH2:37][CH2:36][CH:35](O)[CH2:34][CH2:33]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH:35]2[CH2:36][CH2:37][O:32][CH2:33][CH2:34]2)=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 2773621p-Tert-butoxyphenolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 712121564-(4-tert-butoxyphenoxy)tetrahydro-2H-pyranYield 85.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Tert-butoxyphenol (200 mg, 1.203 mmole) and PPh3 (410 mg, 1.564 mmole) were combined in toluene (5 mL). To this was added tetrahydro-2H-pyran-4-ol (0.149 mL, 1.564 mmole). DIAD (0.304 mL, 1.564 mmole) was added dropwise at RT. After stirring overnight the mixture was concentrated. Flash column chromatography (Biotage-SNAP-25 g SiO2, 10% EtOAc/hexanes) gave 4-(4-tert-butoxyphenoxy)tetrahydro-2H-pyran (257 mg, 85%) as a clear oil. 1H NMR (400 MHz, CDCl3): 06.90 (d, J=8.9 Hz, 2 H); 6.83-6.79 (m, 2 H); 4.39 (m, 1 H); 4.03-3.95 (m, 2 H); 3.56 (m, 2 H); 2.04-1.96 (m, 2 H); 1.83-1.72 (m, 2 H); 1.30 (s, 9 H).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-a01ef0f946434be3bc9474f507c3c7e9
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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