Triphenylphosphine → HCID 86651273, compound

HRID 1515004Notes

Reaction equation

HRID 1515004 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1.[CH3:12][C:13]1([CH3:20])[O:17][C@H:16]([CH2:18]O)[CH2:15][O:14]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:12][C:13]1([CH3:20])[O:17][C@H:16]([CH2:18][O:1][C:2]2[CH:3]=[C:4]([CH3:11])[C:5]([CH:6]=[O:7])=[C:8]([CH3:10])[CH:9]=2)[CH2:15][O:14]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5910722,6-Dimethyl-4-hydroxybenzaldehydeHCID 736056(R)-SolketalHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 86651273HCID 86651273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxy-2,6-dimethylbenzaldehyde (150 mg, 1.0 mmol) and ((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (132 mg, 1.0 mmol) in THF (10 mL) was added PPh3-resin (553 mg, 2.13 mmol/g) and DEAD (0.54 mL of a 40% solution, 1.2 mmol) and the suspension was stirred at ambient temperature overnight. The reaction mixture was filtered and partioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the organic layer was dried with MgSO4, filtered and concentrated. Purification by flash chromatography using heptane/EtOAc (2:1) as eluent gave 4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2,6-dimethylbenzaldehyde as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-443023a437974b25be68e5239cb7f718
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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