Water → HCID 86754092, compound

HRID 1415911Notes

Reaction equation

HRID 1415911 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:16](/[C:29](/[CH3:39])=[CH:30]\[CH:31]=[CH:32]\[C:33](\[CH3:38])=[CH:34]\[C:35]([OH:37])=[O:36])=[CH:17][C:18]2[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=2[CH:24]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>C1COCC1>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:16](/[C:29](/[CH3:39])=[CH:30]\[CH:31]=[CH:32]\[C:33](\[CH3:38])=[CH:34]\[C:35]([OH:37])=[O:36])=[CH:17][C:18]2[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=2[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86754093HCID 86754093, compound

Product 1

HCID 86754092HCID 86754092, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of (E,E,Z)-7-{3-[5-(tert-butyldimethylsilyloxy)pentyloxy]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl}-3-methyl-2,4,6-octatrienoic acid (850 mg, 1.5 mmol) and a 1M solution in THF of tetrabutylammonium fluoride (TBAF) (3.1 ml) in THF (10 ml) was stirred at room temperature for 1 h and then treated with ethyl acetate and with water. After settling, the organic phase was separated and washed twice with water, dried over anhydrous magnesium sulfate and concentrated in a rotary evaporator under vacuum at 40° C.

Workup

  1. customthe organic phase was separated
  2. washwashed twice with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in a rotary evaporator under vacuum at 40° C.

Sources & evidence

ORD record
ord-fbded6499f304f4c941a89aac0e4601d
Source dataset
uspto-grants-1999_06
Patent number
US05910508

Reaction notes

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