Ethanol → 6-Ethynyl-1-(iso-propyl-methyl-amino)-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene

HRID 427799Notes

Reaction equation

[CH:1]1([N:4]2[CH2:13][C:12]([CH3:15])([CH3:14])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH:16]=O)[CH:10]=3)[CH2:5]2)[CH2:3][CH2:2]1.[CH2:18](O)[CH3:19].[OH-].[Na+].O1CCC[CH2:24]1>>[C:16]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[CH:5]([N:4]([CH:1]([CH3:2])[CH3:3])[CH3:13])[CH2:19][CH2:18][C:12]2([CH3:14])[CH3:15])#[CH:24]

Participants

Reactant 4

HCID 702Ethanol

HCID 8028Tetrahydrofuran

HCID 14798Sodium Hydroxide

HCID 225689542-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carbaldehyde2×

Product 1

HCID 225689626-Ethynyl-1-(iso-propyl-methyl-amino)-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene

Procedure

Following general procedure I and using 4-[5-(iso-propyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-ylethynyl)]-benzoic acid ethyl ester (Compound 25, 0.04 g, 0.01 mmol), ethanol (2 mL), tetrahydrofuran (1 mL) and 1M aqueous sodium hydroxide solution (1 mL) followed by recrystallization from diethylether-hexane, the title compound was obtained as an off-white solid (0.010 g, 27%).

Workup

customfollowed by recrystallization from diethylether-hexane

Sources & evidence

ORD record: ord-62ce7a2d471b4518899c2d664a08cc8b
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313107B1

Reaction notes

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