1,1,1-Trimethoxy-2-methylpropane → HCID 10081181, compound

HRID 1769046Notes

Reaction equation

HRID 1769046 reaction equation
[CH3:1][O:2][C:3](OC)(OC)[CH:4]([CH3:6])[CH3:5].[OH:11][C@H:12]([CH2:14][C@@H:15]([OH:17])[CH3:16])[CH3:13].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>[CH:4]([C:3]1([O:2][CH3:1])[O:17][C@H:15]([CH3:16])[CH2:14][C@@H:12]([CH3:13])[O:11]1)([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 404951,1,1-Trimethoxy-2-methylpropaneHCID 69502002,4-Pentanediol, (+)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 10081181HCID 10081181, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 1140TolueneSolvent

Procedure

A mixture of 15.6 g (0.105 mol) of 1,1,1-trimethoxyisobutane, 10 g (0.0962 mol) of 2(S),4(S)-dihydroxypentane, and 251 mg of PPTS in 150 ml of toluene (dried over 3° A sieves) was allowed to reflux under argon for 11/2 hours while azeotroping water formed using the Dean-Stark trap. The reaction mixture was cooled, 1.2 g of potassium tert. butoxide was added, and the solvent was distilled. Ether (100 ml) was added to the residue, passed through a supercel pad eluting with 300 ml of ether, and the combined solvent was distilled in vacuo (<40° C.). The residue was distilled to afford 14.3 g (79.4%) of 2-isopropyl-2-methoxy-4(R),6(R)-dimethyl-1,3-dioxane, b.p. 78°-82° C./15 mm.

Workup

  1. customdried over 3° A sieves)
  2. temperatureto reflux under argon for 11/2 hours
  3. customwhile azeotroping water
  4. customformed
  5. temperatureThe reaction mixture was cooled
  6. distillationthe solvent was distilled
  7. additionEther (100 ml) was added to the residue
  8. washeluting with 300 ml of ether
  9. distillationthe combined solvent was distilled in vacuo (<40° C.)
  10. distillationThe residue was distilled

Sources & evidence

ORD record
ord-1feb61bdb4a84daf91ea3334aaf86745
Source dataset
uspto-grants-1995_01
Patent number
US05380729

Reaction notes

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