Dimethoxymethane → HCID 67095505, compound

HRID 1470049Notes

Reaction equation

HRID 1470049 reaction equation
[OH:1][C@:2]1([C:12]([OH:14])=[O:13])[CH2:6][CH2:5][C:4]([CH2:8][OH:9])([CH3:7])[C:3]1([CH3:11])[CH3:10].[CH3:15]OCOC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:7][C:4]12[C:3]([CH3:11])([CH3:10])[C@@:2]([C:12]([OH:14])=[O:13])([CH2:6][CH2:5]1)[O:1][CH2:15][O:9][CH2:8]2

Participants

5

Reactant 3

HCID 8020Dimethoxymethane2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 66858910HCID 66858910, compound

Product 1

HCID 67095505HCID 67095505, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of Example 222A (131.6 mg), dimethoxymethane (0.575 mL) and para-toluenesulfonic acid monohydrate (catalytic) in benzene (15 mL) was stirred and heated to reflux with a Dean-Stark trap overnight. An additional 0.5 mL dimethoxymethane was added and heating continued 24 hours. The reaction mixture was evaporated to dryness and flash chromatographed over silica gel eluting with 10% methanol/CH2Cl2 to afford the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 0.88 (s, 3H), 0.94 (s, 3H), 1.15 (s, 3H), 1.88-2.05 (m, 3H), 2.7-2.85 (m, 1H), 3.59 (s, 2H), 5.00 (AB q, J=26.3, 7.9 Hz, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux with a Dean-Stark trap overnight
  3. temperatureheating
  4. customThe reaction mixture was evaporated to dryness and flash
  5. customchromatographed over silica gel eluting with 10% methanol/CH2Cl2

Sources & evidence

ORD record
ord-d209ad4bd38449ec8694770a714e96fd
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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