Diethyl Ether → HCID 19106995, compound

HRID 1197549Notes

Reaction equation

HRID 1197549 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-c7dc94b1214e40c1b818179da4047bbc
Source dataset
uspto-grants-1994_01
Patent number
US05276053

Reaction notes

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