Diethyl Ether → (E)-11(methoxyethoxymethoxy)-2-undecen-1-ol

HRID 1741985Notes

Reaction equation

HRID 1741985 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]/[C:28](OCC)=[O:29].CO.O.CCOCC>C1COCC1>[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]/[CH2:28][OH:29]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 21225700Diisobutylaluminumhydride2×HCID 22242641Methanol--water (1/1)HCID 131718635Ethyl (E)-11-(methoxyethoxymethoxy)-2-undecenoate

Product 1

HCID 19009407(E)-11(methoxyethoxymethoxy)-2-undecen-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 mmol of diisobutylaluminum hydride (DIBAH) (1.2 molar solution in toluene) are added with exclusion of moisture to a solution of 1 mmol of 3 in 20 ml of THF (abs.) at such a rate that the temperature does not exceed 40° C. The mixture is stirred at room temperature for 2 hours. Excess DIBAH is carefully hydrolyzed by means of methanol/H2O, the mixture is stirred for 20 minutes, and ether is added. The precipitate is filtered off with suction and washed several times with ether. The solution is dried over MgSO4, and the solvent is removed in vacuo. The product is purified by flash chromatography (PE/CH2Cl2)

Workup

  1. customdoes not exceed 40° C
  2. stirringthe mixture is stirred for 20 minutes
  3. filtrationThe precipitate is filtered off with suction
  4. washwashed several times with ether
  5. dry with materialThe solution is dried over MgSO4
  6. customthe solvent is removed in vacuo
  7. customThe product is purified by flash chromatography (PE/CH2Cl2)

Sources & evidence

ORD record
ord-bc32d335e529471f92fb77265f3239cc
Source dataset
uspto-grants-1994_08
Patent number
US05336436

Reaction notes

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