Water → HCID 58982097, compound

HRID 1182475Notes

Reaction equation

HRID 1182475 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1)=[O:18])C.O.[OH-].[Na+]>CCOCC>[OH:18][CH:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][OH:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 10881518ETHYL 8-(2-NAPHTHYL)-8-OXOOCTANOATEHCID 21226445Aluminium lithium hydride

Product 1

HCID 58982097HCID 58982097, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (114 mg, 3.00 mmol) was added to diethyl ether (3 mL) at 0° C. A solution of ethyl-7-(2-naphthoyl)-heptanoate 49 g (312 mg, 1.00 mmol) in ether (2 mL) was added dropwise at 0° C. and the reaction mixture was stirred at 0° C. for 1 hour, then at room temperature for 1 hour. Deionized water was added slowly dropwise (5 mL) followed by 2N NaOH (5 mL). The mixture was filtered through a short pad of Celite, washing with ether. The organic layer was separated and dried (MgSO4). The solvents were removed in vacuo to give the title compound 70 (247 mg, 91%). 1H NMR (400 MHz, DMSO-d6): δ 7.83 (m, 4H), 7.45 (m, 3H), 5.22 (m, 1H), 4.64 (m, 1H), 4.28 (m, 1H), 3.35 (m, 2H), 1.68 (m, 2H), 1.37 (m, 2H), 1.22 (m, 8H).

Workup

  1. waitat room temperature for 1 hour
  2. filtrationThe mixture was filtered through a short pad of Celite
  3. washwashing with ether
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-f75da1098ed04700b9bc2f5ed25011cc
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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