Hydrochloric Acid → HCID 9823687, compound

HRID 2186552

Reaction equation

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

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 1.084 g of methyl (E)-5-[2-(3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-vinyl]-thiophene-2-carboxylate (from Example 8.1) in 15 ml ethanol was treated with a solution of 2.77 g KOH in 8 ml H20, followed by the addition of 7 ml THF. The mixture was stirred at 45° C. for 2.5 hours. The reaction mixture was diluted with 40 ml water and acidified to pH 2 with HCl 25%. The mixture was extracted with 4 portions of 50 ml of ethyl acetate. The combined extracts were washed with 50 ml water and 50 ml of aqueous saturated sodium chloride solution. Drying (MgSO4), filtration and concentration in vacuo gave a pale yellow solid. Trituration in pentane and filtration afforded 952 mg of the title product as a pale yellow solid. M.p. 164-165° C.

Workup

extractionThe mixture was extracted with 4 portions of 50 ml of ethyl acetate
washThe combined extracts were washed with 50 ml water and 50 ml of aqueous saturated sodium chloride solution
customDrying
filtration(MgSO4), filtration and concentration in vacuo
customgave a pale yellow solid
filtrationTrituration in pentane and filtration

Sources & evidence

ORD record: ord-6e63a5d210d9481eb8b147b7c1eb0ddf
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403810B2

Linked notes

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