Sodium Iodide → 22-iododocosanoic Acid

HRID 544416

반응식

HRID 544416 반응식
[C:1]([OH:24])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22].C1(BC2CCCCC2)CCCCC1.C([O-])(=O)C.[Na+].[I-:43].[Na+].CC1C=CC(S(NCl)(=O)=O)=CC=1>>[I:43][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:24])=[O:23]

참가 물질

6

반응물 5

HCID 5238Sodium IodideHCID 31388TosylchloramideHCID 517045Sodium AcetateHCID 443400421-Docosenoic acidHCID 15879360CID 15879360

생성물 1

HCID 987639122-iododocosanoic Acid

실험 절차

21-Docosenoic acid (55mg. 0.16 mmol) was hydroborated with dicyclohexylborane (0.32 mmol) at 0° C. The organoborane was iodinated with a mixture of sodium aceate (0.32 mmol), sodium iodide (0.16 mmol), and chloramine-T (0.32 mmol). The product was isolated by a column chromotography on silica gel (10% ethyl acetate:hexane):yield 68 mg (91%); mp 71°-2° C.; m/e 466.5 (calcd 466.5); NMR (CDCl3), 1.2 δ (s, 36H, alkane), 2.1 (m, 4H, --CH2 --CO2H and --CH2CH2I), 3.0 (t, 2H, --CH2I, 11.9 (s, 1H, --CO2H).

후처리

  1. customThe product was isolated by a column chromotography on silica gel (10% ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-e824cab9876c419ea204dc475ae04813
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04450149

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