Diethyl Ether → HCID 19106995, compound

HRID 1460602Notes

Reaction equation

HRID 1460602 reaction equation
[H-].[Na+].O1[C:7]2([CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][OH:14])[CH2:8]2)OCC1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC[O:25][CH2:26][CH3:27].[O:28]1CC[CH2:30][CH2:29]1>>[C:16]1([CH2:15][O:14][CH2:13][CH:9]2[CH2:8][CH2:7][C:12]3([C:29](=[O:28])[CH2:30][CH2:27][C:26]3=[O:25])[CH2:11][CH2:10]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 588050HCID 588050, compound

Product 1

HCID 19106995HCID 19106995, compoundYield 85%

Procedure

To a solution of sodium hydride (2.5 g, 105 mmole) in dry tetrahydrofuran (150 ml) was added via an addition funnel a solution of the 1,4-dioxaspiro[4.5]decan-7-methanol (Berkowitz, W. F., et al, J. Org. Chem., 1987, 52, 1119), (15 g, 87.1 mmol) and dry tetrahydrofuran (25 ml). After stirring 30 minutes, benzylbromide (11.4 ml, 95.8 mmol) was added. The mixture was stirred for 4 days at room temperature. The reaction mixture was poured onto water and the organics layered with ether. The ether layer was dried (MgSO4), concentrated in vacuo, and chromatographed to give 19.4 g (85% yield) of the title compound as a colorless oil.

Workup

  1. stirringThe mixture was stirred for 4 days at room temperature
  2. additionThe reaction mixture was poured onto water
  3. dry with materialThe ether layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customchromatographed

Sources & evidence

ORD record
ord-75f45c411c214aa8ba7b5d429327937c
Source dataset
uspto-grants-1991_12
Patent number
US05071853

Reaction notes

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