Aluminium lithium hydride → HCID 67936567, compound

HRID 1085630Notes

Reaction equation

HRID 1085630 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:10][C:11]1[C:12]([O:35][CH3:36])=[C:13]([C:17](=[O:34])[CH2:18][CH2:19][C:20]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=2)=[O:21])[S:14][C:15]=1[CH3:16])[CH:8]=[CH2:9]>O1CCCC1>[CH2:7]([O:10][C:11]1[C:12]([O:35][CH3:36])=[C:13]([CH:17]([OH:34])[CH2:18][CH2:19][CH:20]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=2)[OH:21])[S:14][C:15]=1[CH3:16])[CH:8]=[CH2:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23056683HCID 23056683, compound

Product 1

HCID 67936567HCID 67936567, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (100 mg) was added to a solution of 1-(4-allyloxy-3-methoxy-5-methyl-thiophenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione (1.0 g, 2.2 mmol) in tetrahydrofuran (10 ml) at 0° C. The mixture was stirred at room temperature for 0.5 hour and quenched with 2 N sodium hydroxide. The cake was filtered and washed with THF-Et2O (1:1, v/v). The combined filtrates were evaporated to give 1-(4-allyloxy-3-methoxy-5-methylthiophenyl)-4-(3,4,5-trimethoxyphenyl)-1,4- butanediol, which was used directly in the next experiment without further purification. The title compound had n.m.r. (CDCl3): δ 0.88 (b, CH2CH2), 2.43 (s, SCH3), 3.85, 3.86, 3.87 (3s, 4 OCH3), 4.54 (d, CH2CH=CH2), 4.72 (b, 2 CHOH), 5.22-5.45 (CH2CH=CH2), 6.16 (m, CH2CH-CH2), 6.60, 6.74 (2s, ArH).

Workup

  1. customquenched with 2 N sodium hydroxide
  2. filtrationThe cake was filtered
  3. washwashed with THF-Et2O (1:1
  4. customThe combined filtrates were evaporated

Sources & evidence

ORD record
ord-5e54659dde12420a98bdfcb11a302472
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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