Sodium Bicarbonate → HCID 53794764, compound

HRID 568878Notes

Reaction equation

HRID 568878 reaction equation
[Br-].COC(C)([O:6][CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C([Li])CCC.[C:35]1([CH2:41][O:42][C:43]2[CH:44]=[C:45]([CH:48]=[C:49]([O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH:50]=2)[CH:46]=O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)(O)[O-].[Na+]>C1COCC1.O.Cl>[C:53]1([CH2:52][O:51][C:49]2[CH:48]=[C:45]([CH:46]=[CH:9][CH2:8][CH2:7][OH:6])[CH:44]=[C:43]([O:42][CH2:41][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:50]=2)[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5613513,5-DibenzyloxybenzaldehydeHCID 10950828Phosphonium, [3-(1-methoxy-1-methylethoxy)propyl]triphenyl-, bromideHCID 178418339Butyllithium

Product 1

HCID 53794764HCID 53794764, compoundYield 58.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A stirred suspension of [3-(1-methoxy-1-methylethoxy)propyl](triphenylphosphonium)bromide (4 g) in dry THF (25 ml) at 0° C. was heated with butyl lithium (5.28 ml) and the mixture stirred at 0° C. for 10 min. 3,5-Bis(phenylmethoxy)benzaldehyde (2.24 g) in dry THF (15 ml) was added and the mixture stirred for a further 45 min at room temperature under nitrogen, diluted with ER (100 ml) and filtered through silica (20 g) twice. The filtrate was evaporated in vacuo to give a yellow oil which was dissolved in a mixture of THF (50 ml), water (5 ml) and 2M hydrochloric acid (1 ml) and left at room temperature for 30 min. The mixture was basified with sodium bicarbonate solution and extracted with ER (200 ml). The organic phase was washed with water (150 ml), brine (100 ml), dried and evaporated in vacuo to give a yellow oil. Purification by FCC eluting with ER-CX (3:2) gave a colourless oil (1.48 g). T.l.c. (ER-CX 3:1) Rf 0.26

Workup

  1. stirringthe mixture stirred for a further 45 min at room temperature under nitrogen
  2. additiondiluted with ER (100 ml)
  3. filtrationfiltered through silica (20 g) twice
  4. customThe filtrate was evaporated in vacuo
  5. customto give a yellow oil which
  6. waitleft at room temperature for 30 min
  7. extractionextracted with ER (200 ml)
  8. washThe organic phase was washed with water (150 ml), brine (100 ml)
  9. customdried
  10. customevaporated in vacuo
  11. customto give a yellow oil
  12. customPurification by FCC
  13. washeluting with ER-CX (3:2)

Sources & evidence

ORD record
ord-004c6c7d24d5455488fd82eeb388077e
Source dataset
uspto-grants-1988_03
Patent number
US04730008

Reaction notes

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