Sodium hydride → HCID 54028008, compound

HRID 1578821Notes

Reaction equation

HRID 1578821 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH2:13][CH2:14][CH:15]=[C:16]([CH3:28])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:27])[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[C:5](=[O:12])[CH2:6]C(OCC)=O.Br[CH2:30][C:31]([CH3:58])=[CH:32][CH2:33][CH2:34][C:35]([CH3:57])=[CH:36][CH2:37][CH2:38][C:39]([CH3:56])=[CH:40][CH2:41][CH2:42][C:43]([CH3:55])=[CH:44][CH2:45][CH2:46][C:47]([CH3:54])=[CH:48][CH2:49][O:50]C(=O)C>CCOCC>[CH3:54][C:47]([CH2:46][CH2:45][CH:44]=[C:43]([CH3:55])[CH2:42][CH2:41][CH:40]=[C:39]([CH3:56])[CH2:38][CH2:37][CH:36]=[C:35]([CH3:57])[CH2:34][CH2:33][CH:32]=[C:31]([CH3:58])[CH2:30][CH2:6][C:5](=[O:12])[CH:4]([CH3:3])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:28])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:27])[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[CH:48][CH2:49][OH:50]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53653006HCID 53653006, compoundHCID 53771714HCID 53771714, compound

Product 1

HCID 54028008HCID 54028008, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of sodium hydride (2.64 g) in ether (100 ml), a solution of ethyl 3,7,11,15-tetramethyl-6,10,14-hexadecatrien-2-one-1-carboxylate (18.1 g) in ether (18 ml) is dropwise added, and the resulting mixture is dropwise added, and the resulting mixture is stirred for 30 minutes. Then, a solution of 1-bromo-2,6,10,14,18-pentamethyl-20-acetoxy-2,6,10,14,18-eicosapentaene (26 g) in ether (26 ml) is dropwise added thereto. The reaction mixture is poured into ice water. The ether layer is washed with water, dried and evaporated. The residual material is treated as in Example 1 (4) to give 3,7,11,15,19,23,27,31, 35-nonamethyl-2,6,10,14,18,26,30,34-hexatriacontaoctaen-22-on-1-ol (29 g). IR: 3400, 1000 cm-1 (OH); 1705 cm-1 (C=O); 1668 cm-1 (C=C). NMR (carbon tetrachloride): δ 1.59 (s), 1.66 (s), 2.01 (m), 2.7 (m), 4.1 (m), 5.05 (m).

Workup

  1. additionthe resulting mixture is dropwise added
  2. washThe ether layer is washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-4caf35bf369f4b73a0769d288ac5d802
Source dataset
uspto-grants-1976_02
Patent number
US03939202

Reaction notes

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