HCID 131733395, compound → HCID 86678087, compound

HRID 2274711Notes

Reaction equation

HRID 2274711 reaction equation
[Si]([O:8][CH:9]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:39]\[CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:10][CH:11]([OH:30])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(C(C)(C)C)(C)C.[SiH3]O[SiH3]>Cl.CO.CCO>[CH3:47][CH2:46][CH2:45][CH2:44][CH2:43]/[CH:42]=[CH:41]\[CH2:40]/[CH:39]=[CH:38]\[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH:9]([OH:8])[CH2:10][CH:11]([OH:30])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 1

HCID 131733395HCID 131733395, compound

Product 1

HCID 86678087HCID 86678087, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

The silyl ether (6Z,9Z,29Z,32Z)-21-((tert-butyldimethylsilyl)oxy)octatriaconta-6,9,29,32-tetraen-19-ol (6) (2.44 g, 3.62 mmol) was dissolved in HCl—CH3OH (1%, 100 mL) and EtOH (40 mL). After stirring (45 min) the solution was concentrated and subjected to chromatography (10%→15% EtOAc-hexanes) to yield (6Z,9Z,29Z,32Z)-octatriaconta-6,9,29,32-tetraene-18,20-diol (7) (1.54 g, 76%) as a clear colorless oil. Rf 0.12 (10% EtOAc-hexanes), FW 558.96, C38H70O2.

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-6386d0c3e4a14b87b691a0de1f583b67
Source dataset
uspto-grants-2015_09
Patent number
US09126966B2

Reaction notes

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