Hydrochloric Acid → HCID 18177877, compound

HRID 394919Notes

Reaction equation

C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][CH:12]([C:18]2[CH:27]=[CH:26][C:25]3[C:24]([CH3:29])([CH3:28])[CH2:23][CH2:22][C:21]([CH3:31])([CH3:30])[C:20]=3[CH:19]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1.[OH-].[K+].C1COCC1.Cl>C(O)C.O>[CH3:28][C:24]1([CH3:29])[CH2:23][CH2:22][C:21]([CH3:30])([CH3:31])[C:20]2[CH:19]=[C:18]([CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:11]#[C:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:32])=[O:2])=[CH:5][CH:6]=3)[CH:27]=[CH:26][C:25]1=2

Participants

Conditions

Temperature: 45 °C

Procedure

The ester (609 mg) was dissolved in 9 ml of ethanol and treated with 1.59 g of potassium hydroxide in 6 ml of water. The heterogeneous mixture was further treated with 4 ml of THF and the resulting clear solution was heated to 45° C. for 1.5 hour. The mixture was diluted with 20 ml of water and the pH was adjusted to 2 with HCl 25%. The mixture was extracted with 3 portions of 25 ml of ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The resulting orange oil was purified by flash chromatography (SiO2, 25% ethyl/hexanes) followed by trituration in pentane, giving 290 mg of (RS)-4-[3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-oct-1-ynyl]-benzoic acid as a white solid, m.p. 115-116° C.

Workup

extractionThe mixture was extracted with 3 portions of 25 ml of ethyl acetate
dry with materialThe combined organic extracts were dried over MgSO4
concentrationconcentrated in vacuo
customThe resulting orange oil was purified by flash chromatography (SiO2, 25% ethyl/hexanes)

Sources & evidence

ORD record: ord-b503304f6bc3474785810ece1bb232e7
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603012B2

Reaction notes

Loading…