Water → HCID 18546260, compound

HRID 1267770Notes

Reaction equation

HRID 1267770 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([C:15]([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:35][CH:34]=1)([CH:18]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:24][C:23]=1[OH:32])[CH2:19][CH:20]=[CH2:21])[CH2:16]O)[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1(C)C=CC=CC=1.O1CCOCC1>[CH2:13]([C:15]1([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:35][CH:34]=2)[CH:18]([CH2:19][CH:20]=[CH2:21])[C:22]2[C:23](=[CH:24][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:26][CH:27]=2)[O:32][CH2:16]1)[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18546255HCID 18546255, compound

Product 1

HCID 18546260HCID 18546260, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

A 40% solution of diethyl azodicarboxylate in toluene (21.9 ml) was added dropwise to an ice-cold solution of (2RS,3RS)-2-ethyl-3-(2-hydroxy-4-methoxymethoxyphenyl)-2-(4-methoxymethoxy-phenyl)-5-hexenol (9.5 g) and triphenylphosphine (15.0 g) in dry 1,4-dioxane (150 ml) over 25 minutes under nitrogen atmosphere. The reaction mixture was stirred for 10 minutes on ice and for 30 minutes at room temperature. Under ice-cooling, water was added to the reaction mixture, which was then extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate and then concentrated to give a crude product, which was then purified by flash column chromatography (silica gel: Merck Kieselgel 60, eluent: hexane/ethyl acetate=50/1→20/1→10/1) to give (3RS,4RS)-3-ethyl-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-(2-propenyl)chroman (8.4 g, Yield 92.6%) as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. extractionwas then extracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a crude product, which
  6. customwas then purified by flash column chromatography (silica gel: Merck Kieselgel 60, eluent: hexane/ethyl acetate=50/1→20/1→10/1)

Sources & evidence

ORD record
ord-a90dbecf60ce4fb28b67faadee71213b
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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