Methanol → HCID 22252718, compound

HRID 1612016Notes

Reaction equation

HRID 1612016 reaction equation
COCCOC[O:7][C:8]1[C:9]([Se:22][C:23]2[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=2)=[CH:10][C:11]2[C:12]([CH3:21])([CH3:20])[CH2:13][CH2:14][C:15]([CH3:19])([CH3:18])[C:16]=2[CH:17]=1.S(=O)(=O)(O)O.CO>C1COCC1>[OH:7][C:8]1[C:9]([Se:22][C:23]2[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=2)=[CH:10][C:11]2[C:12]([CH3:20])([CH3:21])[CH2:13][CH2:14][C:15]([CH3:19])([CH3:18])[C:16]=2[CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 87929924HCID 87929924, compound

Product 1

HCID 22252718HCID 22252718, compoundYield 108.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4-(3-methoxyethoxymethoxy5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylselanyl)benzoate (2.3 g, 4.4 mmol), concentrated sulphuric acid (475 μl), methanol (40 ml) and THF (20 ml)is stirred for 48 h at room temperature. The reaction medium is extracted with ethyl ether. The organic phase is washed twice with water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum. The product is purified by crystallization from heptane. 2.06 g (97%) of the expected compound are obtained in the form of an orange-coloured powder. m.p.=113° C.

Workup

  1. extractionThe reaction medium is extracted with ethyl ether
  2. washThe organic phase is washed twice with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated on a rotary evaporator under vacuum
  5. customThe product is purified by crystallization from heptane

Sources & evidence

ORD record
ord-1d2a716e082a40c6bf046f72eff204b2
Source dataset
uspto-grants-2006_01
Patent number
US06992094B1

Reaction notes

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