Water → HCID 22033228, compound

HRID 1267489Notes

Reaction equation

HRID 1267489 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][O:22][CH3:23])[CH:17]=[CH:16][C:15]=1[CH:24]([CH2:39][CH:40]=[CH2:41])[C:25]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][O:37][CH3:38])=[CH:31][CH:30]=1)([CH3:28])[CH2:26]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCOCC1>[CH3:23][O:22][CH2:21][O:20][C:18]1[CH:19]=[C:14]2[C:15]([CH:24]([CH2:39][CH:40]=[CH2:41])[C:25]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH2:36][O:37][CH3:38])=[CH:33][CH:34]=3)([CH3:26])[CH2:28][O:13]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18546297HCID 18546297, compound

Product 1

HCID 22033228HCID 22033228, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Diethyl azodicarboxylate (5.94 ml) was added dropwise to an ice-cold solution of (2RS,3RS)-3-(2-hydroxy-4-methoxymethoxyphenyl)-2-(4-methoxymethoxyphenyl)-2-methyl-5-hexen-1-ol (6.9 g) and triphenylphosphine (11.24 g) in anhydrous 1,4-dioxane (120 ml) over 25 minutes under nitrogen atmosphere. The reaction mixture was stirred for 20 minutes at room temperature. 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 concentrated to give a crude product, which was then purified by flash column chromatography (silica gel: Merck Kieselgel 60, eluent: hexane/ethyl acetate=100/1→20/1→9/1) to give (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-(2-propenyl)chroman (6.5 g, Yield 98.6%) as a colorless oil.

Workup

  1. extractionwas then extracted twice with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customto give a crude product, which
  5. customwas then purified by flash column chromatography (silica gel: Merck Kieselgel 60, eluent: hexane/ethyl acetate=100/1→20/1→9/1)

Sources & evidence

ORD record
ord-d59963edfad34d0c9dea3edc8a0c79ba
Source dataset
uspto-grants-2003_04
Patent number
US06552069B1

Reaction notes

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