Hydrochloric Acid → HCID 14835753, compound

HRID 1709069Notes

Reaction equation

HRID 1709069 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[CH:8]=[CH:9][CH2:10]Cl)=[O:4].C([O:19][AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].Cl>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)/[CH:8]=[CH:9]/[CH2:10][OH:19])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 16684435Lithium tritertbutoxyaluminohydrideHCID 54136437HCID 54136437, compound

Product 1

HCID 14835753HCID 14835753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-Methoxycarbonylcinnamyl chloride (24 g) was dissolved in dry tetrahedrofuran and then this solution added to lithium tri-tert-butoxyaluminohydride (63.5 g) dissolved in tetrahydrofuran (250 ml) at -78° C. The resultant clear solution was stirred at -78° C. for 30 minutes then it was added to ice and 2M hydrochloric acid (750 ml). The two phase mixtures was extracted 4 times with dichloromethane. After drying the dichloromethane was evaporated to yield the title compound as a pale yellow oil.

Workup

  1. extractionThe two phase mixtures was extracted 4 times with dichloromethane
  2. dry with materialAfter drying the dichloromethane
  3. customwas evaporated

Sources & evidence

ORD record
ord-6e925a3bc44c4b6c920be713b179fa70
Source dataset
uspto-grants-1990_08
Patent number
USRE033300

Reaction notes

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