Water → HCID 54391081, compound

HRID 344829Notes

Reaction equation

HRID 344829 reaction equation
C([SnH](CCCC)CCCC)CCC.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH:22]=[CH:23][C:24](=[O:33])[CH2:25][CH:26]([OH:32])[CH2:27][C:28]([O:30][CH3:31])=[O:29].O.CCOCC>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH2:22][CH2:23][C:24](=[O:33])[CH2:25][CH:26]([OH:32])[CH2:27][C:28]([O:30][CH3:31])=[O:29]

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 5948TributylstannaneHCID 54438093HCID 54438093, compound

Product 1

HCID 54391081HCID 54391081, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tributyltin hydride (450 μL, 1.7 mmol) was added dropwise over 1-1/2 hours to a stirred solution of the ene-one ester from Step A (320 mg, 1 mmol) and tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.03 mmol) in dry THF (5 mL) at ambient temperature under N2. After standing at 20° C. overnight the light-brown solution was distributed between water (100 mL) and ether (150 mL). The organic layer was separated and washed with water (2×100 mL), dried and evaporated. The residual oil (1 major spot on TLC with Rf 0.39 vis-a-vis 0.35 for the starting ene-one ester on Whatman MK6F silica using CHCl3 -MeOH; 99:1 as eluent) was chromatographed on a Still column to obtain the product (260 mg, 81%) as a pale amber gum; NMR (CDCl3) δ: 2.5-2.525 (2H, m, --C2CO2 --), 2.57-2.73 (2H, m, -- COC2C(OH)--), 2.77 (2H, t, J=7.5 Hz, AR-CH2CH2CO-), 2.98 (2H, t, J=7.5 Hz, Ar-CH2CH2CO-), 3.71 (3H, s, --CO2C3), 4.45-4.51 (H, m, --CH(OH)--).

Workup

  1. customThe organic layer was separated
  2. washwashed with water (2×100 mL)
  3. customdried
  4. customevaporated
  5. custom99:1 as eluent) was chromatographed on a Still column

Sources & evidence

ORD record
ord-a2988361192e43a7b1d4931903aedf2f
Source dataset
uspto-grants-1991_10
Patent number
US05053525

Reaction notes

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