Triphenylphosphine → HCID 59527457, compound

HRID 384461Notes

Reaction equation

HRID 384461 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH2:13]([O:20][C:21]1[CH:22]=[C:23](O)[CH:24]=[CH:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:13]([O:20][C:21]1[CH:26]=[C:25]([CH:24]=[CH:23][CH:22]=1)[O:12][CH2:11][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 138048Benzyl 3-hydroxyphenyl etherHCID 100808381,4-Dioxaspiro[4.5]decan-8-ylmethanol

Product 1

HCID 59527457HCID 59527457, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,4-dioxaspiro[4.5]dec-8-ylmethanol (946 mg), 3-(benzyloxy)phenol (1 g), and triphenylphosphine (1.57 g) in THF (15 mL) was added azodicarboxylate diethyl (944 μL) under ice-cooling, and the mixture was stirred at room temperature overnight. The reaction liquid was concentrated under reduced pressure, benzene was added to the residue, and insolubles were removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=92/8-85/15) to obtain 8-{[3-(benzyloxy)phenoxy]methyl}-1,4-dioxaspiro[4.5]decane (846 mg).

Workup

  1. temperaturecooling
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure, benzene
  4. additionwas added to the residue, and insolubles
  5. customwere removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=92/8-85/15)

Sources & evidence

ORD record
ord-4933b62320a240a682f2a75a0ba4f2d8
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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