Solketal → HCID 22321972, compound

HRID 1006466Notes

Reaction equation

HRID 1006466 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:31][C:32]1([CH3:39])[O:36][CH:35]([CH2:37]O)[CH2:34][O:33]1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:37][CH:35]2[CH2:34][O:33][C:32]([CH3:39])([CH3:31])[O:36]2)[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 7528SolketalHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

Product 1

HCID 22321972HCID 22321972, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6.64 g (35.0 mmol) A1, 10.03 g (38.0 mmol) triphenylphosphine and 5.06 g (38.0 mmol) (rac)-2,2-dimethyl-[1,3]-dioxolane-4-methanol in 100 ml dry tetrahydrofurane a solution of 6.48 g (37.0 mmol) diethyl azodicarboxylate in 20 ml dry tetrahydrofurane was added and the mixture was stirred at room temperature overnight. After removal of the solvent and column chromatography on SiGel (hexane/ethyl acetate 4:1) 6.12 g (57%) A8 were obtained as a colorless oil that solidified on ice standing.

Workup

  1. customAfter removal of the solvent and column chromatography on SiGel (hexane/ethyl acetate 4:1) 6.12 g (57%) A8
  2. customwere obtained as a colorless oil that

Sources & evidence

ORD record
ord-ba35e7eecb3a4d2a859f886e6d534137
Source dataset
uspto-grants-2004_09
Patent number
US06790852B2

Reaction notes

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