Hydrochloric Acid → HCID 53799581, compound

HRID 274889Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[C:11]1([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[O:23][CH2:22][C:21]([C:27]([CH3:34])=[CH:28][C:29](OCC)=[O:30])=[CH:20]3)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].Cl>O1CCCC1.C(OCC)C>[C:11]1([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[O:23][CH2:22][C:21]([C:27]([CH3:34])=[CH:28][CH2:29][OH:30])=[CH:20]3)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3.47 g (98 mmol) of lithium aluminium hydride are added to a solution, which is kept at 0° C. and under argon, of 4.95 g (37 mmol) of sublimed anhydrous aluminium chloride and 50 ml of diethyl ether. The resulting complex is stirred at 0° C. for 20 minutes, and then a solution of 11.9 g (37.1 mmol) of the ester obtained in Step D in 130 ml of a mixture of diethyl ether and tetrahydrofuran (10:3) is added rapidly. The whole is kept at 0° C. for 45 minutes. The excess hydride is decomposed by the addition, in succession, of 10 ml of 0.4N hydrochloric acid, 10 ml of 1N hydrochloric acid and 20 ml of 4N hydrochloric acid. After dilution with 100 ml of water, the reaction mixture is extracted with diethyl ether (from 500 to 2000 ml). The ethereal phases are treated in the customary manner, yielding a pale yellow liquid which is used directly in the following step without additional purification.

Workup

waitThe whole is kept at 0° C. for 45 minutes
extractionAfter dilution with 100 ml of water, the reaction mixture is extracted with diethyl ether (from 500 to 2000 ml)
additionThe ethereal phases are treated in the customary manner
customyielding a pale yellow liquid which
customis used directly in the following step without additional purification

Sources & evidence

ORD record: ord-93eca7f3bcdc4e87b71e2a6414c78d12
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05391569

Reaction notes

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