Diethyl Ether → HCID 53749929, compound

HRID 1578822Notes

Reaction equation

HRID 1578822 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:47])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:46])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:45])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:44])[CH2:22][CH2:23][C:24](=[O:43])[CH:25]([CH3:42])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:41])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:40])[CH2:34][CH2:35][CH:36]=[C:37]([CH3:39])[CH3:38])=[CH:3][CH2:4][OH:5].[CH3:48][C:49](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:50].CCOCC>N1C=CC=CC=1>[C:49]([O:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:47])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:46])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:45])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:44])[CH2:22][CH2:23][C:24](=[O:43])[CH:25]([CH3:42])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:41])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:40])[CH2:34][CH2:35][CH:36]=[C:37]([CH3:39])[CH3:38])(=[O:50])[CH3:48]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 54028008HCID 54028008, compound

Product 1

HCID 53749929HCID 53749929, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,26,30,34-hexatriacontaoctaen-22-on-1-ol 6.5 g) in pyridine (1 g), acetic anhdyride (3.0 g) is added, and the resulting mixture is allowed to stand at room temperature for 5 hours. The reaction mixture is poured into ice water and shaken with ether. The ether layer is washed with water, dried and evaporated. The residual material (6.5 g) is chromatographed on silica gel (70 g) using benzene to give 1-acetoxy-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,26,30,34-hexatriacontaoctaen-22-one (6.1 g). A solution of this compound in ethanol (6 ml) is dropwise added to a solution of sodium borohydride (0.1 g) in ethanol (10 ml) while cooling with ice, and stirring is continued for 3 hours. The reaction mixture is poured into an aqueous saturated solution of ammonium chloride and extracted with ether. The ether extract is washed with water, dried and concentrated. The residual material (4.8 g) is treated as in Example 1 (5) a) to give 1-acetoxy-3,7,11,15,19,23,27,31, 35-nonamethyl-2,6,10,14,18,26,30,34-hexatriacontaoctaen- 22-ol (2.1 g) as a fraction (1) and 3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,26,30,34-hexatriacontaoctaene-1,22-diol (0.9 g) as a fraction (2). The latter is treated with acetic anhydride as above to give 1-acetoxy-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,26,30,34-hexatriacontaoctaen-22-ol (0.82 g).

Workup

  1. washThe ether layer is washed with water
  2. customdried
  3. customevaporated
  4. customThe residual material (6.5 g) is chromatographed on silica gel (70 g)

Sources & evidence

ORD record
ord-733ce2a9d41f4529b0bb1701073e1d0a
Source dataset
uspto-grants-1976_02
Patent number
US03939202

Reaction notes

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