Hydrochloric Acid → HCID 88424876, compound

HRID 1728993Notes

Reaction equation

HRID 1728993 reaction equation
[C@@H:1]12[CH2:9][C@@H:5]([C:6]1([CH3:8])[CH3:7])[CH2:4][C@@H:3](/[CH:10]=[CH:11]\[CH:12]([CH:14]1OCC[O:15]1)[CH3:13])[C@H:2]2[CH3:19].Cl>C1COCC1>[CH3:13]/[C:12](=[CH:11]\[CH2:10][C@H:3]1[CH2:4][C@H:5]2[CH2:9][C@H:1]([C:6]2([CH3:8])[CH3:7])[C@@H:2]1[CH3:19])/[CH:14]=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67789737HCID 67789737, compound

Product 1

HCID 88424876HCID 88424876, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 18.1 g (68.6 mmol) of the dioxolane of Example 8, 250 ml of THF and 120 ml of 4N HCl is stirred for 4 days at room temperature (monitoring by gas chromatography) and is then poured into 250 ml of ice-cold water. After extraction with 3×200 ml of ethyl ether, drying (MgSO4) and evaporation of the solvents there are obtained 19 g of crude oil which is purified by flash chromatography on silica (eluent: petroleum ether+1% ethyl ether) to give 10.5 g of (E)-2-methyl-4-[(1S,2R,3S,5S)-3-pinanyl]-2-butenal (yield=70%).

Workup

  1. extractionAfter extraction with 3×200 ml of ethyl ether
  2. customdrying
  3. custom(MgSO4) and evaporation of the solvents
  4. customthere are obtained 19 g of crude oil which
  5. customis purified by flash chromatography on silica (eluent: petroleum ether+1% ethyl ether)

Sources & evidence

ORD record
ord-14c2afa685f14272b1e4d5125f93294c
Source dataset
uspto-grants-1994_07
Patent number
US05329052

Reaction notes

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