Triphenylphosphine → 6-(Oxan-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 63628

Reaction equation

HRID 63628 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[O:13]1[CH2:18][CH2:17][CH:16]([CH2:19]O)[CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:13]1[CH2:18][CH2:17][CH:16]([CH2:19][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2773573(Oxan-4-yl)methanolHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 623855006-(Oxan-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-oneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6-hydroxy-1-tetralone (2.0 g, 12.4 mmol), tetrahydropyran-4-methanol (1.7 g, 14.8 mmol) and triphenylphosphine (6.5 g, 24.7 mmol) in THF (40 mL) was added DEAD (4.3 g, 24.7 mmol) at 0° C. The reaction was stirred at rt overnight. The solution was concentrated and purified by silica gel chromatography (PE:EtOAc=12:1) to give 3.2 g (100%) of the title compound as a yellow oil. [M+H] Calc'd for C16H20O3, 261. Found, 261.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by silica gel chromatography (PE:EtOAc=12:1)

Sources & evidence

ORD record
ord-a3e9c38cd19541998fbfff7ca47a3bdd
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Linked notes

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