HCID 13151114, compound → HCID 13151115, compound

HRID 127556Notes

Reaction equation

HRID 127556 reaction equation
[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[C:5]#[C:6][CH:7]([OH:17])[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].N([O-])=O.[Na+]>O.[Pt]=O.C(O)C>[CH2:19]([O:18][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][CH:7]([OH:17])[CH2:8][O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:20]

Participants

6

Reactant 2

HCID 13151114HCID 13151114, compound2×HCID 23668193Sodium Nitrite

Product 1

HCID 13151115HCID 13151115, compoundYield 204%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 5-benzyloxy-4-hydroxy-2-pentynal diethyl acetal (43.2 g) in abs. ethanol (250 ml) is hydrogenated in the presence of 82.7% platinum oxide (1.4 g), sodium nitrite (14 mg) and 1 drop of water for 90 minutes in a Parr hydrogenation apparatus. The reaction is repeated exactly as above with another (43.2 g) portion of 5-benzyloxy-4-hydroxy-2-pentynal diethyl acetal; the two mixtures are combined and the catalyst is removed by filtration through a bed of celite and washed with ethanol. The combined filtrate is evaporated in vacuo to give a residue (89.4 g, 100%). A 200 mg portion of the residue is purified on Quantagram PQ1F plates (developed in 40% CHCl3 /hexane three successive times). The principal band is eluted with ethyl acetate and the solvent is evaporated in vacuo to give 5-benzyloxy-4-hydroxypentanal diethyl acetate (152 mg); ir (neat) 2.88 μ (OH); nmr (CDCl3,δ): 1.17 (t, 6 H, OCH2CH3), 1.62 (m, 4H, CHCH2CH2CH), 2.7 (b, 1H, >CH-OH), 3.53 (m, 7H, OCH2CH3 and OCH2CH and ##STR6## 4.47 (m, 1H, >CHOH), 4.5 (s, 2H φCH2O), 7.28 (s, 5H, φCH2O).

Workup

  1. customthe catalyst is removed by filtration through a bed of celite
  2. washwashed with ethanol
  3. customThe combined filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-fdc0f3ebdb62495e9d4c4014a9afa1cb
Source dataset
uspto-grants-1981_03
Patent number
US04256644

Reaction notes

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