Sodium hydride → HCID 14805470, compound

HRID 1493113Notes

Reaction equation

HRID 1493113 reaction equation
[H-].[Na+].CN1C(=O)N(C)CCC1.C1(C)C=CC(S(O[CH2:22][CH2:23][CH2:24][CH:25]([CH3:34])[CH2:26][CH:27]([OH:33])[CH:28]=[CH:29][C:30]([CH3:32])=[CH2:31])(=O)=O)=CC=1>C(COC)OC>[CH3:34][CH:25]1[CH2:24][CH2:23][CH2:22][O:33][CH:27](/[CH:28]=[CH:29]/[C:30]([CH3:32])=[CH2:31])[CH2:26]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 53892004HCID 53892004, compound

Product 1

HCID 14805470HCID 14805470, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

The procedure described in Example 1 h) was carried on with 2.68 g of NaH (111 mmole) in 130 ml of monoglyme, 3.80 ml of DMPU (31.6 mmole) and 8.52 g (24 mmole) of the above-mentioned p-toluenesulfonate in monoglyme (130 ml). After purification of 5.1 g of crude product, 3.0 g of a more than 98% pure mixture, containing two diastereoisomeric forms (ca. 1:1) of (E)-4-methyl-2-(3-methyl-1,3-butadienyl)oxepane were obtained. P.b. 111°-112°/14.67×102Pa; yield: 69%. The two diastereoisomers were separated by repeated preparative gas chromatography.

Workup

  1. customdescribed in Example 1 h
  2. customAfter purification of 5.1 g of crude product, 3.0 g of a more than 98% pure mixture
  3. additioncontaining two diastereoisomeric forms (ca. 1:1) of (E)-4-methyl-2-(3-methyl-1,3-butadienyl)oxepane
  4. customwere obtained
  5. custom111°-112°/14.67×102Pa
  6. customThe two diastereoisomers were separated

Sources & evidence

ORD record
ord-3a85e8d955b24df0a450f4efd8cf5f5f
Source dataset
uspto-grants-1991_06
Patent number
US05021402

Reaction notes

Loading…