Trimethyl orthoformate → HCID 19855426, compound

HRID 1650052Notes

Reaction equation

HRID 1650052 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:14]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:13][CH2:12][C:11](=[O:19])[CH2:10]1.[CH3:20]OC(OC)OC>S(=O)(=O)(O)O.CO>[CH3:20][O:19][C:11]12[CH2:12][CH2:13][CH:14]([CH2:15][CH2:16][CH2:17][OH:18])[CH:9]([CH2:10]1)[C:3]1[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=1[O:1]2

Participants

5

Reactant 2

HCID 9005Trimethyl orthoformateHCID 70360050(3R,4R)-3-(2,4-Dihydroxyphenyl)-4-(3-hydroxypropyl)cyclohexan-1-one

Product 1

HCID 19855426HCID 19855426, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.5 g. (5.68 mmole) of trans-3-(2,4-dihydroxyphenyl)-4-(3-hydroxypropyl)cyclohexanone in 40 ml. methanol, 6 ml. trimethylorthoformate and 7 drops of concentrated sulfuric acid was stirred at 0° C. for 45 minutes. The reaction was quenched by the addition of excess solid sodium bicarbonate and then evaporated on a rotovapor. The residue was diluted with 300 ml. saturated sodium bicarbonate-300 ml. ether. The ether extract was dried over magnesium sulfate and evaporated. The crude product was purified via column chromatography on 150 g. of silica gel eluted in 15 ml. fractions with ether to yield 1.29 g. (82%) of the title compound as an oil.

Workup

  1. customThe reaction was quenched by the addition of excess solid sodium bicarbonate
  2. customevaporated on a rotovapor
  3. additionThe residue was diluted with 300 ml
  4. extractionThe ether extract
  5. dry with materialwas dried over magnesium sulfate
  6. customevaporated
  7. customThe crude product was purified via column chromatography on 150 g
  8. washof silica gel eluted in 15 ml
  9. customfractions with ether to yield 1.29 g

Sources & evidence

ORD record
ord-ef8edd9a516e44a5baba73f5a675b9f5
Source dataset
uspto-grants-1990_05
Patent number
US04921994

Reaction notes

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