HCID 18349870, compound → HCID 22091595, compound

HRID 1648687Notes

Reaction equation

HRID 1648687 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:21])=[CH:15]/[C:16](OCC)=[O:17])[CH:5]=[CH:4][C:3]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH3:1][C:2]1([CH3:22])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:21])=[CH:15]/[CH2:16][OH:17])[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 18349870HCID 18349870, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 22091595HCID 22091595, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ester 34 (4.10 g, 14.3 mmol) in anhydrous diethyl ether (40 mL) was added via cannula over 10 min to a slurry of lithium aluminum hydride (0.33 g, 8.6 mmol) in diethyl ether (100 mL) at 0° C. under argon. After 2 h, additional lithium aluminum hydride (0.13 g, 3.4 mmol) was added, and the mixture was stirred for 5 h. The reaction was quenched by sequential addition of H2O (0.46 mL), 15% aqueous sodium hydroxide (0.46 mL), and H2O (1.38 mL). The resulting slurry was filtered and the filtrate was concentrated in vacuo to give 3.8 g of a colorless oil. Purification by column chromatography (30:1 ratio silica gel/crude product; elution with 10% to 15% ethyl acetate/hexanes) provided 3.51 g (95%) of 35 as a colorless oil. 1H NMR (300 MHz, CDCl3) δ7.35 (d, J=2 Hz, 1H, ArH), 7.28 (d, J=8 Hz, 1H, ArH), 7.18 (dd, J=2, 8 Hz, 1H, ArH), 5.95 (t, J=5 Hz, 1H, C=CH), 435 (t, J=5 Hz, 2H, CH2OH), 2.10 (s, 3H, CH3C=C), 1.65 (s, 4H, CH2CH2), 1.30 (s, 6H, 2×CH3), and 1.28 (s, 6H, 2×CH3).

Workup

  1. customThe reaction was quenched by sequential addition of H2O (0.46 mL), 15% aqueous sodium hydroxide (0.46 mL), and H2O (1.38 mL)
  2. filtrationThe resulting slurry was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-288116315da145d294efcc5c0f8d2e6b
Source dataset
uspto-grants-1995_07
Patent number
US05436369

Reaction notes

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