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Sodium Bicarbonate → HCID 53794764, 화합물

HRID 568878
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HRID 568878 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

HCID 53794764HCID 53794764, 화합물수율 58.4%

시약·촉매·용매 3

HCID 313
Hydrochloric Acid
용매
HCID 962Water용매
HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-004c6c7d24d5455488fd82eeb388077e
출처 데이터셋
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04730008

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