HCID 19097835, compound → HCID 19097837, compound

HRID 486325Notes

Reaction equation

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

Participants

Reactant 2

HCID 19097835HCID 19097835, compound

HCID 57264371HCID 57264371, compound

Product 1

HCID 19097837HCID 19097837, compoundYield 31%

Procedure

Following the procedure described in Singh, A. & Schnur, J. M., Synthetic Comm. 16, 847 (1986), 1-iodo-4-oxa-tetradecyne (10 mmol) was coupled with 9-oxa-11-dodecynoic acid (1.98 g, 10 mmol) to produce 1.2 g 9,16-dioxa-hexacosa-11,13-diynoic acid (31% yield). The 9-oxa-11-dodecynoic acid was dissolved in aqueous KOH solution (1.1 mol eq.). CuCl (0.25 mol eq.) in ethylamine (70% aq. solution) was added, followed by 15 mg±5 mg hydroxyl amine hydrochloride NH2OH.HCl crystals. To this solution (yellow) was then added, in small portions, the 1-iodo-4-oxa-tetradecyne dissolved in 10 ml of CH3OH--CH3CH2OCH2CH3 (1:1). On addition of 1-iodo-4-oxa-tetradecyne the reaction mixture turned blue, and then yellow on addition of a few drops of 10% aqueous NH2OH.HCl solution.

Sources & evidence

ORD record: ord-e251de548c274444a4744cbe2a62843d
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05290960

Reaction notes

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