4-Hydroxybenzaldehyde → HCID 16220388, compound

HRID 2377274Notes

Reaction equation

HRID 2377274 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C([NH+](CC)CC)C.[CH2:23](O)[C:24]#[CH:25].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O.N>CO>[CH2:25]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1)[C:24]#[CH:23]

Participants

9

Reactant 7

HCID 1264-HydroxybenzaldehydeHCID 222AmmoniaHCID 7859Propargyl alcoholHCID 8083MorpholineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1385867Triethylammonium

Product 1

HCID 16220388HCID 16220388, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (500 mg, 4.09 mmol) and morpholine (356 mg, 4.09 mmol) in methanol (10 mL) was added macroporous triethylammonium methylpolystyrene borohydride (2.0 g, 6.0 mmol) and the mixture was stirred at ambient temperature for about 2 days. The mixture was filtered and concentrated under vacuum. The residue was dissolved in tetrahydrofuran (20 mL) and to this solution was added propargyl alcohol (229 mg, 4.09 mmol), diphenylphosphino-polystyrene (5.1 g, 8.18 mmol) and diethyl azodicarboxylate (1.06 g, 6.13 mmol). After stirring overnight at room temperature, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by flash chromatography on silica gel using diethyl ether/n-pentane (1:3) as eluent to provide Example 635. MS (DCI-NH3): m/z 232 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in tetrahydrofuran (20 mL) and to this solution
  4. stirringAfter stirring overnight at room temperature
  5. filtrationthe mixture was filtered
  6. concentrationthe filtrate was concentrated under vacuum
  7. customThe residue was purified by flash chromatography on silica gel
  8. customto provide Example 635

Sources & evidence

ORD record
ord-f8c0d22819474dbb8b15c3760afeff31
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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