2,2-Dimethoxypropane → HCID 67126622, compound

HRID 2040341Notes

Reaction equation

HRID 2040341 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][C:13]([CH2:18][OH:19])([CH2:16][OH:17])[CH2:12][CH2:11]1)(C(C)(C)C)(C)C.CO[C:22](OC)([CH3:24])[CH3:23].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CN(C)C=O>[CH3:23][C:22]1([CH3:24])[O:17][CH2:16][C:13]2([CH2:12][CH2:11][CH:10]([CH2:9][OH:8])[CH2:15][CH2:14]2)[CH2:18][O:19]1

Participants

6

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 67168685HCID 67168685, compound

Product 1

HCID 67126622HCID 67126622, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EXAMPLE 391D (1 g) and 2,2-dimethoxypropane (1.276 mL) in N,N-dimethylformamide (6.93 mL) was added para-toluenesulfonic acid monohydrate (1.451 g). The reaction was stirred for 4 hours at room temperature, triethylamine was added and the solution was concentrated by rotary evaporation. The residue was placed under high vacuum overnight to remove N,N-dimethylformamide. The residue was purified by regular phase flash column chromatography (Analogix—0-100% hexanes/ethyl acetate).

Workup

  1. concentrationthe solution was concentrated by rotary evaporation
  2. customwas placed under high vacuum overnight
  3. customto remove N,N-dimethylformamide
  4. customThe residue was purified by regular phase flash column chromatography (Analogix—0-100% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-78ed286d6199447bb1bae646c9425c85
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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