Potassium Sodium Tartrate → HCID 18177821, compound

HRID 394922Notes

Reaction equation

C([O:3][C:4](=O)[CH:5]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:6]1[CH:15]=[CH:14][C:13]2[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]([CH3:19])([CH3:18])[C:8]=2[CH:7]=1)C.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>CCOCC.CCCCCC.O>[CH2:21]([O:20][CH:5]([C:6]1[CH:15]=[CH:14][C:13]2[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]([CH3:18])([CH3:19])[C:8]=2[CH:7]=1)[CH2:4][OH:3])[CH2:22][CH2:23][CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

3.4 g of (RS)-butoxy-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetic acid ethyl ester were dissolved in 40 ml of ether. After the dropwise addition of 30 ml of a 1M solution of DIBAH in hexane at −78° C., the reaction mixture was warmed to 0° C. and stirred at this temperature for 1.5 hours. For work up, the solution was cooled to −10° C., carefully treated with 1 ml of a 2 molar solution of Rochelle salt in water followed by addition of further 7 ml of this reagent. The resulting white suspension was stirred at room temperature for 1.5 hours, filtered, the residue washed well with ether and the combined organic solution dried (MgSO4) and the solvent evaporated to give 3.05 g of (RS)-2-butoxy-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanol as colorless oil. It was used in the next step without further purification.

Workup

temperatureFor work up, the solution was cooled to −10° C.
stirringThe resulting white suspension was stirred at room temperature for 1.5 hours
filtrationfiltered
washthe residue washed well with ether
dry with materialthe combined organic solution dried (MgSO4)
customthe solvent evaporated

Sources & evidence

ORD record: ord-cecf4bdd447f4ba1bb5ac4e75f4fb0b7
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603012B2

Reaction notes

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