HCID 131719272, compound → HCID 131719274, compound

HRID 1781566Notes

Reaction equation

HRID 1781566 reaction equation
[Si:1]([O:8][C:9]1[C:17]([CH2:18]/[CH:19]=[C:20](\[CH3:39])/[CH:21]([CH2:28][CH2:29][CH2:30][O:31][Si](C(C)(C)C)(C)C)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]([O:40][CH3:41])[C:15]([CH3:42])=[C:14]2[C:10]=1[C:11](=[O:43])[O:12][CH2:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(#N)C>[Si:1]([O:8][C:9]1[C:17]([CH2:18]/[CH:19]=[C:20](\[CH3:39])/[CH:21]([CH2:28][CH2:29][CH2:30][OH:31])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]([O:40][CH3:41])[C:15]([CH3:42])=[C:14]2[C:10]=1[C:11](=[O:43])[O:12][CH2:13]2)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 131719272HCID 131719272, compound

Product 1

HCID 131719274HCID 131719274, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Ethyl (E) 6-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy -7-methyl-3-oxo-isobenzofuran-5-yl)-3-(3-tert-butyldimethylsilyloxypropyl) -4-methylhex-4-enoate (2.92 g) was dissolved in acetonitrile (50 ml). To this was added a solution of 40% aqueous HF (5 ml) in acetonitrile (45 ml), and the reaction mixture stirred for 10 minutes. Most of the acetonitrile was then evaporated, and the remaining solution diluted with ether. The ether was washed with water, saturated sodium bicarbonate (3×), brine, and dried. Evaporation of the solvent gave an oil which was chromatographed on silica gel (40% ethyl acetate in hexanes) to give ethyl (E) 6-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxo-isobenzofuran -5-yl)-3-(3-hydroxypropyl)-4-methylhex-4-enoate (2.10 g) , a compound of Formula 803, as an oil.

Workup

  1. customMost of the acetonitrile was then evaporated
  2. additionthe remaining solution diluted with ether
  3. washThe ether was washed with water, saturated sodium bicarbonate (3×), brine
  4. customdried
  5. customEvaporation of the solvent
  6. customgave an oil which
  7. customwas chromatographed on silica gel (40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-836ced56c8c24fdfb72bfddef7a5f7f9
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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