alpha-Ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol → Methyl n-tert-butoxycarbonyl-4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]-2-pyrrolecarboxylate

HRID 840459Notes

Reaction equation

HRID 840459 reaction equation
[C:1]([CH:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8]([CH3:18])([CH3:17])[C:7]=2[CH:6]=1)[OH:4])#[CH:2].[C:19]([O:23][C:24]([N:26]1[CH:30]=[C:29](I)[CH:28]=[C:27]1[C:32]([O:34][CH3:35])=[O:33])=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24]([N:26]1[CH:30]=[C:29]([C:2]#[C:1][CH:3]([OH:4])[C:5]2[CH:14]=[CH:13][C:12]3[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8]([CH3:18])([CH3:17])[C:7]=3[CH:6]=2)[CH:28]=[C:27]1[C:32]([O:34][CH3:35])=[O:33])=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 11817362alpha-Ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanolHCID 544637781-tert-butyl 2-methyl 4-iodo-1H-pyrrole-1,2-dicarboxylate

Product 1

HCID 54193334Methyl n-tert-butoxycarbonyl-4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]-2-pyrrolecarboxylateYield 99.5%

Procedure

Following the basic procedure of Example 11(d), by reacting 2 g (8.2 mmol) of α-ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol with 3 g (8.5 mmol) of methyl N-tert-butoxycarbonyl-4-iodo-2-pyrrolecarboxylate, 3.8 g (98%) of the expected ester were obtained in the form of a brown oil.

Sources & evidence

ORD record
ord-08aea7b807e04eada00d93cf76623c4c
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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